# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Aitipamula, Srinivasulu' _publ_contact_author_email 'srinivasulu aitipamula@ices.a-star.edu.sg' _publ_section_title ; Solvates and polymorphic phase transformations of 2-chloro-4-nitrobenzoic acid ; loop_ _publ_author_name S.Aitipamula P.Chow R.Tan # Attachment '- CEC-CIF.txt' data_CNBA-Hydrate _database_code_depnum_ccdc_archive 'CCDC 782719' #TrackingRef '- CEC-CIF.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '2-chloro-4-nitrobenzoic acid hydrate' ; _chemical_name_common "'2-chloro-4-nitrobenzoic acid hydrate'" _chemical_melting_point ? _chemical_formula_moiety 'C7 H4 Cl N O4, H2 O' _chemical_formula_sum 'C7 H6 Cl N O5' _chemical_formula_weight 219.58 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 7.2871(15) _cell_length_b 7.9395(16) _cell_length_c 8.5516(17) _cell_angle_alpha 117.58(3) _cell_angle_beta 95.80(3) _cell_angle_gamma 93.48(3) _cell_volume 433.0(2) _cell_formula_units_Z 2 _cell_measurement_temperature 118(2) _cell_measurement_reflns_used 1698 _cell_measurement_theta_min 2.7164 _cell_measurement_theta_max 30.7238 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.684 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 224 _exptl_absorpt_coefficient_mu 0.436 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8803 _exptl_absorpt_correction_T_max 0.9101 _exptl_absorpt_process_details 'R. H. Blessing, Acta Cryst. 1995 A51, 33-38' _exptl_special_details ; ? ; _diffrn_ambient_temperature 118(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 5920 _diffrn_reflns_av_R_equivalents 0.0158 _diffrn_reflns_av_sigmaI/netI 0.0127 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.83 _diffrn_reflns_theta_max 28.27 _reflns_number_total 2116 _reflns_number_gt 2070 _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^)+(0.0353P)^2^+0.1968P] 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 2116 _refine_ls_number_parameters 139 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0292 _refine_ls_R_factor_gt 0.0287 _refine_ls_wR_factor_ref 0.0741 _refine_ls_wR_factor_gt 0.0736 _refine_ls_goodness_of_fit_ref 1.082 _refine_ls_restrained_S_all 1.082 _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 0.13081(4) 1.10511(4) 0.86616(4) 0.02519(10) Uani 1 1 d . . . O1 O -0.29084(13) 1.00461(12) 0.78994(12) 0.02429(19) Uani 1 1 d . . . O2 O -0.33943(13) 0.68998(12) 0.69938(12) 0.02374(19) Uani 1 1 d . . . O4 O 0.48272(12) 0.73720(14) 0.33227(13) 0.0272(2) Uani 1 1 d . . . O3 O 0.27799(13) 0.54899(13) 0.10507(12) 0.0264(2) Uani 1 1 d . . . N1 N 0.32323(13) 0.66186(14) 0.26454(13) 0.0195(2) Uani 1 1 d . . . C6 C -0.12656(15) 0.63743(16) 0.42763(15) 0.0177(2) Uani 1 1 d . . . H6 H -0.2422 0.5580 0.3888 0.021 Uiso 1 1 calc R . . C2 C 0.07835(15) 0.90901(15) 0.65615(14) 0.0169(2) Uani 1 1 d . . . C7 C -0.25072(15) 0.84388(16) 0.70693(15) 0.0179(2) Uani 1 1 d . . . C3 C 0.21777(15) 0.86336(16) 0.54894(15) 0.0182(2) Uani 1 1 d . . . H3 H 0.3369 0.9366 0.5901 0.022 Uiso 1 1 calc R . . C4 C 0.17729(15) 0.70743(16) 0.37994(15) 0.0166(2) Uani 1 1 d . . . C5 C 0.00772(15) 0.59291(16) 0.31530(15) 0.0181(2) Uani 1 1 d . . . H5 H -0.0157 0.4877 0.1983 0.022 Uiso 1 1 calc R . . C1 C -0.09496(15) 0.79705(15) 0.59709(14) 0.0163(2) Uani 1 1 d . . . O5 O 0.40150(13) 0.72896(14) 0.89451(12) 0.02344(19) Uani 1 1 d . . . H1 H -0.428(3) 0.722(3) 0.767(3) 0.049(6) Uiso 1 1 d . . . H2 H 0.382(3) 0.828(3) 0.979(3) 0.050(6) Uiso 1 1 d . . . H4 H 0.418(3) 0.654(3) 0.941(3) 0.047(5) 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 0.03081(17) 0.02117(16) 0.01609(14) 0.00347(11) 0.00166(11) -0.00166(11) O1 0.0317(5) 0.0190(4) 0.0251(4) 0.0104(4) 0.0134(4) 0.0095(3) O2 0.0260(4) 0.0194(4) 0.0288(5) 0.0114(4) 0.0152(4) 0.0055(3) O4 0.0174(4) 0.0330(5) 0.0350(5) 0.0183(4) 0.0080(3) 0.0048(3) O3 0.0339(5) 0.0219(4) 0.0223(4) 0.0078(4) 0.0135(4) 0.0034(4) N1 0.0209(5) 0.0183(5) 0.0244(5) 0.0127(4) 0.0094(4) 0.0062(4) C6 0.0168(5) 0.0173(5) 0.0181(5) 0.0074(4) 0.0034(4) 0.0024(4) C2 0.0215(5) 0.0145(5) 0.0143(5) 0.0066(4) 0.0017(4) 0.0026(4) C7 0.0201(5) 0.0192(5) 0.0163(5) 0.0093(4) 0.0046(4) 0.0052(4) C3 0.0175(5) 0.0183(5) 0.0203(5) 0.0107(4) 0.0016(4) 0.0010(4) C4 0.0172(5) 0.0175(5) 0.0185(5) 0.0103(4) 0.0062(4) 0.0055(4) C5 0.0194(5) 0.0167(5) 0.0166(5) 0.0064(4) 0.0031(4) 0.0031(4) C1 0.0182(5) 0.0163(5) 0.0167(5) 0.0090(4) 0.0045(4) 0.0048(4) O5 0.0282(4) 0.0208(4) 0.0204(4) 0.0075(4) 0.0111(3) 0.0032(3) _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 1.7307(14) . ? O1 C7 1.2109(15) . ? O2 C7 1.3182(14) . ? O2 H1 0.88(2) . ? O4 N1 1.2260(14) . ? O3 N1 1.2300(15) . ? N1 C4 1.4710(14) . ? C6 C5 1.3866(16) . ? C6 C1 1.3984(17) . ? C6 H6 0.9500 . ? C2 C3 1.3890(16) . ? C2 C1 1.3998(16) . ? C7 C1 1.5007(15) . ? C3 C4 1.3860(17) . ? C3 H3 0.9500 . ? C4 C5 1.3854(16) . ? C5 H5 0.9500 . ? O5 H2 0.82(2) . ? O5 H4 0.86(2) . ? 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 C7 O2 H1 110.2(14) . . ? O4 N1 O3 123.69(10) . . ? O4 N1 C4 118.44(10) . . ? O3 N1 C4 117.87(10) . . ? C5 C6 C1 121.22(11) . . ? C5 C6 H6 119.4 . . ? C1 C6 H6 119.4 . . ? C3 C2 C1 120.89(10) . . ? C3 C2 Cl1 117.14(9) . . ? C1 C2 Cl1 121.95(9) . . ? O1 C7 O2 124.47(11) . . ? O1 C7 C1 123.37(11) . . ? O2 C7 C1 112.15(10) . . ? C4 C3 C2 117.76(11) . . ? C4 C3 H3 121.1 . . ? C2 C3 H3 121.1 . . ? C5 C4 C3 123.43(11) . . ? C5 C4 N1 118.74(10) . . ? C3 C4 N1 117.83(10) . . ? C4 C5 C6 117.58(11) . . ? C4 C5 H5 121.2 . . ? C6 C5 H5 121.2 . . ? C6 C1 C2 119.04(11) . . ? C6 C1 C7 118.36(10) . . ? C2 C1 C7 122.59(10) . . ? H2 O5 H4 103(2) . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 28.27 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.370 _refine_diff_density_min -0.241 _refine_diff_density_rms 0.048 #====END data_CNBA-1,4-dioxane _database_code_depnum_ccdc_archive 'CCDC 782720' #TrackingRef '- CEC-CIF.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '1,4-dioxane solvate of 2-chloro-4-nitrobenzoic acid' ; _chemical_name_common "'1,4-dioxane solvate of 2-chloro-4-nitrobenzoic acid'" _chemical_melting_point ? _chemical_formula_moiety 'C7 H4 Cl N O4, 0.5(C4 H8 O2)' _chemical_formula_sum 'C9 H8 Cl N O5' _chemical_formula_weight 245.61 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.0000 '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 6.918(3) _cell_length_b 8.368(3) _cell_length_c 9.714(3) _cell_angle_alpha 106.777(2) _cell_angle_beta 93.774(4) _cell_angle_gamma 108.433(5) _cell_volume 503.1(3) _cell_formula_units_Z 2 _cell_measurement_temperature 136(2) _cell_measurement_reflns_used 1499 _cell_measurement_theta_min 2.2232 _cell_measurement_theta_max 31.0259 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.621 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 252 _exptl_absorpt_coefficient_mu 0.385 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8835 _exptl_absorpt_correction_T_max 0.9201 _exptl_absorpt_process_details 'R. H. Blessing, Acta Cryst. 1995 A51, 33-38' _exptl_special_details ; ? ; _diffrn_ambient_temperature 136(2) _diffrn_radiation_wavelength 0.71075 _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 7891 _diffrn_reflns_av_R_equivalents 0.0224 _diffrn_reflns_av_sigmaI/netI 0.0247 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.72 _diffrn_reflns_theta_max 31.09 _reflns_number_total 2850 _reflns_number_gt 2649 _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^)+(0.0565P)^2^+0.2312P] 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 2850 _refine_ls_number_parameters 149 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0523 _refine_ls_R_factor_gt 0.0483 _refine_ls_wR_factor_ref 0.1221 _refine_ls_wR_factor_gt 0.1188 _refine_ls_goodness_of_fit_ref 1.142 _refine_ls_restrained_S_all 1.142 _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 0.18359(6) -0.28776(5) 0.04192(4) 0.02910(13) Uani 1 1 d . . . O2 O 0.4069(2) 0.16082(18) 0.44530(14) 0.0322(3) Uani 1 1 d . . . O1 O 0.4633(2) -0.08706(18) 0.32399(13) 0.0342(3) Uani 1 1 d . . . O4 O 0.0840(2) 0.07148(17) -0.29466(13) 0.0320(3) Uani 1 1 d . . . N1 N 0.2088(2) 0.19027(18) -0.19210(15) 0.0249(3) Uani 1 1 d . . . C3 C 0.2080(2) -0.0276(2) -0.06951(16) 0.0218(3) Uani 1 1 d . . . H3 H 0.1449 -0.1206 -0.1595 0.026 Uiso 1 1 calc R . . O3 O 0.2960(2) 0.34247(17) -0.19237(15) 0.0357(3) Uani 1 1 d . . . C4 C 0.2564(2) 0.1495(2) -0.05892(17) 0.0225(3) Uani 1 1 d . . . C2 C 0.2552(2) -0.0644(2) 0.05677(16) 0.0219(3) Uani 1 1 d . . . C1 C 0.3471(2) 0.0728(2) 0.18938(17) 0.0230(3) Uani 1 1 d . . . C6 C 0.3892(3) 0.2489(2) 0.19454(17) 0.0265(3) Uani 1 1 d . . . H6 H 0.4492 0.3425 0.2846 0.032 Uiso 1 1 calc R . . C7 C 0.4092(2) 0.0386(2) 0.32543(17) 0.0253(3) Uani 1 1 d . . . C5 C 0.3447(3) 0.2895(2) 0.06997(18) 0.0263(3) Uani 1 1 d . . . H5 H 0.3740 0.4095 0.0732 0.032 Uiso 1 1 calc R . . O5 O 1.0750(3) 0.64759(18) 0.62932(14) 0.0452(4) Uani 1 1 d . . . C8 C 0.9622(4) 0.4742(3) 0.6316(2) 0.0416(5) Uani 1 1 d . . . H8A H 0.8136 0.4584 0.6262 0.050 Uiso 1 1 calc R . . H8B H 1.0107 0.4614 0.7246 0.050 Uiso 1 1 calc R . . C9 C 1.0111(4) 0.6667(3) 0.4933(2) 0.0410(5) Uani 1 1 d . . . H9A H 1.0947 0.7859 0.4910 0.049 Uiso 1 1 calc R . . H9B H 0.8641 0.6569 0.4842 0.049 Uiso 1 1 calc R . . H1 H 0.442(5) 0.135(4) 0.514(4) 0.063(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 Cl1 0.0352(2) 0.0246(2) 0.0284(2) 0.01064(15) 0.00302(16) 0.01038(16) O2 0.0435(7) 0.0374(7) 0.0193(6) 0.0077(5) 0.0030(5) 0.0208(6) O1 0.0467(7) 0.0403(7) 0.0230(6) 0.0105(5) 0.0026(5) 0.0253(6) O4 0.0362(7) 0.0316(6) 0.0231(6) 0.0088(5) -0.0031(5) 0.0070(5) N1 0.0269(6) 0.0256(6) 0.0232(6) 0.0100(5) 0.0032(5) 0.0092(5) C3 0.0216(7) 0.0248(7) 0.0191(7) 0.0071(5) 0.0033(5) 0.0085(5) O3 0.0427(7) 0.0279(6) 0.0353(7) 0.0165(5) 0.0001(6) 0.0065(5) C4 0.0224(7) 0.0264(7) 0.0204(7) 0.0103(6) 0.0026(5) 0.0085(5) C2 0.0217(7) 0.0237(7) 0.0216(7) 0.0087(5) 0.0049(5) 0.0082(5) C1 0.0226(7) 0.0289(7) 0.0193(7) 0.0091(6) 0.0037(5) 0.0102(6) C6 0.0295(8) 0.0253(7) 0.0202(7) 0.0045(6) 0.0003(6) 0.0073(6) C7 0.0259(7) 0.0309(8) 0.0203(7) 0.0083(6) 0.0040(6) 0.0114(6) C5 0.0265(7) 0.0239(7) 0.0258(8) 0.0076(6) 0.0022(6) 0.0061(6) O5 0.0768(11) 0.0306(7) 0.0226(6) 0.0022(5) -0.0061(6) 0.0204(7) C8 0.0673(14) 0.0350(9) 0.0258(9) 0.0096(7) 0.0040(8) 0.0235(9) C9 0.0677(14) 0.0339(9) 0.0258(9) 0.0093(7) 0.0027(8) 0.0250(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 Cl1 C2 1.7343(17) . ? O2 C7 1.314(2) . ? O2 H1 0.80(3) . ? O1 C7 1.219(2) . ? O4 N1 1.2239(18) . ? N1 O3 1.2256(18) . ? N1 C4 1.4728(19) . ? C3 C4 1.383(2) . ? C3 C2 1.391(2) . ? C3 H3 0.9500 . ? C4 C5 1.383(2) . ? C2 C1 1.399(2) . ? C1 C6 1.394(2) . ? C1 C7 1.495(2) . ? C6 C5 1.389(2) . ? C6 H6 0.9500 . ? C5 H5 0.9500 . ? O5 C8 1.421(3) . ? O5 C9 1.434(2) . ? C8 C9 1.496(3) 2_766 ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C8 1.496(3) 2_766 ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? 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 C7 O2 H1 108(2) . . ? O4 N1 O3 124.14(14) . . ? O4 N1 C4 118.33(13) . . ? O3 N1 C4 117.53(13) . . ? C4 C3 C2 117.43(14) . . ? C4 C3 H3 121.3 . . ? C2 C3 H3 121.3 . . ? C3 C4 C5 123.56(14) . . ? C3 C4 N1 117.96(14) . . ? C5 C4 N1 118.48(14) . . ? C3 C2 C1 121.13(14) . . ? C3 C2 Cl1 116.42(12) . . ? C1 C2 Cl1 122.39(12) . . ? C6 C1 C2 119.09(14) . . ? C6 C1 C7 118.32(14) . . ? C2 C1 C7 122.56(14) . . ? C5 C6 C1 120.98(14) . . ? C5 C6 H6 119.5 . . ? C1 C6 H6 119.5 . . ? O1 C7 O2 123.96(15) . . ? O1 C7 C1 122.80(15) . . ? O2 C7 C1 113.20(14) . . ? C4 C5 C6 117.80(15) . . ? C4 C5 H5 121.1 . . ? C6 C5 H5 121.1 . . ? C8 O5 C9 110.13(15) . . ? O5 C8 C9 111.26(18) . 2_766 ? O5 C8 H8A 109.4 . . ? C9 C8 H8A 109.4 2_766 . ? O5 C8 H8B 109.4 . . ? C9 C8 H8B 109.4 2_766 . ? H8A C8 H8B 108.0 . . ? O5 C9 C8 110.34(16) . 2_766 ? O5 C9 H9A 109.6 . . ? C8 C9 H9A 109.6 2_766 . ? O5 C9 H9B 109.6 . . ? C8 C9 H9B 109.6 2_766 . ? H9A C9 H9B 108.1 . . ? _diffrn_measured_fraction_theta_max 0.887 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.358 _refine_diff_density_min -0.297 _refine_diff_density_rms 0.066 #====END data_CNBA-DMSO _database_code_depnum_ccdc_archive 'CCDC 782721' #TrackingRef '- CEC-CIF.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 'DMSO solvate of 2-chloro-4-nitrobenzoic acid' ; _chemical_name_common "'DMSO solvate of 2-chloro-4-nitrobenzoic acid'" _chemical_melting_point ? _chemical_formula_moiety 'C7 H4 Cl N O4, C2 H6 O S' _chemical_formula_sum 'C9 H10 Cl N O5 S' _chemical_formula_weight 279.69 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' S S 0.1246 0.1234 '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 5.497(3) _cell_length_b 10.408(4) _cell_length_c 10.594(4) _cell_angle_alpha 74.095(15) _cell_angle_beta 81.029(12) _cell_angle_gamma 85.487(16) _cell_volume 575.3(4) _cell_formula_units_Z 2 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 1818 _cell_measurement_theta_min 2.4571 _cell_measurement_theta_max 31.0662 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.39 _exptl_crystal_size_min 0.39 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.614 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 288 _exptl_absorpt_coefficient_mu 0.522 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8028 _exptl_absorpt_correction_T_max 0.8223 _exptl_absorpt_process_details 'R. H. Blessing, Acta Cryst. 1995 A51, 33-38' _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(2) _diffrn_radiation_wavelength 0.71075 _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 8965 _diffrn_reflns_av_R_equivalents 0.0269 _diffrn_reflns_av_sigmaI/netI 0.0251 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 31.09 _reflns_number_total 3283 _reflns_number_gt 3160 _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^)+(0.0493P)^2^+0.5666P] 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 3283 _refine_ls_number_parameters 160 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0502 _refine_ls_R_factor_gt 0.0485 _refine_ls_wR_factor_ref 0.1269 _refine_ls_wR_factor_gt 0.1256 _refine_ls_goodness_of_fit_ref 1.214 _refine_ls_restrained_S_all 1.214 _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 S1 S 0.44001(9) 0.68450(5) 0.93542(5) 0.02097(13) Uani 1 1 d . . . O5 O 0.5028(3) 0.73146(15) 0.78586(14) 0.0247(3) Uani 1 1 d . . . C8 C 0.7267(4) 0.6595(2) 0.9990(2) 0.0275(4) Uani 1 1 d . . . H8A H 0.8268 0.5902 0.9659 0.041 Uiso 1 1 calc R . . H8B H 0.6965 0.6312 1.0961 0.041 Uiso 1 1 calc R . . H8C H 0.8145 0.7432 0.9699 0.041 Uiso 1 1 calc R . . C9 C 0.3286(4) 0.8280(2) 0.9919(2) 0.0259(4) Uani 1 1 d . . . H9A H 0.4554 0.8951 0.9650 0.039 Uiso 1 1 calc R . . H9B H 0.2896 0.8019 1.0888 0.039 Uiso 1 1 calc R . . H9C H 0.1797 0.8657 0.9529 0.039 Uiso 1 1 calc R . . Cl1 Cl 1.25605(9) 0.15156(5) 0.76134(5) 0.02395(13) Uani 1 1 d . . . O4 O 1.3753(3) 0.53940(17) 0.33901(16) 0.0305(3) Uani 1 1 d . . . O3 O 1.0922(3) 0.53787(16) 0.21934(15) 0.0291(3) Uani 1 1 d . . . O2 O 0.6918(3) -0.05122(15) 0.63630(15) 0.0251(3) Uani 1 1 d . . . O1 O 0.8391(3) -0.01978(16) 0.81084(15) 0.0269(3) Uani 1 1 d . . . N1 N 1.1940(3) 0.49156(17) 0.31807(16) 0.0220(3) Uani 1 1 d . . . C4 C 1.0923(3) 0.37185(19) 0.41636(18) 0.0193(3) Uani 1 1 d . . . C6 C 0.8107(3) 0.1968(2) 0.48332(19) 0.0211(4) Uani 1 1 d . . . H6 H 0.6774 0.1535 0.4672 0.025 Uiso 1 1 calc R . . C3 C 1.2022(3) 0.32249(19) 0.53000(18) 0.0198(3) Uani 1 1 d . . . H3 H 1.3372 0.3657 0.5445 0.024 Uiso 1 1 calc R . . C5 C 0.8952(4) 0.3123(2) 0.39075(19) 0.0222(4) Uani 1 1 d . . . H5 H 0.8210 0.3491 0.3128 0.027 Uiso 1 1 calc R . . C7 C 0.8144(3) 0.01561(19) 0.69420(19) 0.0202(3) Uani 1 1 d . . . C1 C 0.9147(3) 0.14189(19) 0.59956(18) 0.0189(3) Uani 1 1 d . . . C2 C 1.1102(3) 0.20831(19) 0.62213(18) 0.0190(3) Uani 1 1 d . . . H1 H 0.640(7) -0.129(4) 0.703(4) 0.059(11) 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 S1 0.0236(2) 0.0195(2) 0.0198(2) -0.00413(17) -0.00276(17) -0.00556(17) O5 0.0319(7) 0.0245(7) 0.0187(6) -0.0053(5) -0.0041(5) -0.0079(6) C8 0.0304(10) 0.0235(9) 0.0308(10) -0.0069(8) -0.0121(8) 0.0009(8) C9 0.0254(9) 0.0235(9) 0.0284(10) -0.0085(8) 0.0007(7) -0.0020(7) Cl1 0.0241(2) 0.0269(2) 0.0204(2) -0.00284(17) -0.00711(16) -0.00268(17) O4 0.0323(8) 0.0293(8) 0.0292(8) -0.0032(6) -0.0049(6) -0.0129(6) O3 0.0348(8) 0.0264(8) 0.0229(7) 0.0005(6) -0.0068(6) -0.0023(6) O2 0.0311(7) 0.0230(7) 0.0216(7) -0.0054(6) -0.0032(6) -0.0069(6) O1 0.0303(7) 0.0282(8) 0.0202(7) -0.0002(6) -0.0045(6) -0.0093(6) N1 0.0258(8) 0.0206(8) 0.0186(7) -0.0044(6) -0.0012(6) -0.0019(6) C4 0.0201(8) 0.0182(8) 0.0182(8) -0.0039(7) 0.0001(6) -0.0008(6) C6 0.0192(8) 0.0243(9) 0.0199(8) -0.0052(7) -0.0029(6) -0.0026(7) C3 0.0193(8) 0.0213(9) 0.0189(8) -0.0064(7) -0.0006(6) -0.0021(6) C5 0.0228(8) 0.0248(9) 0.0193(8) -0.0061(7) -0.0043(7) -0.0002(7) C7 0.0195(8) 0.0214(9) 0.0194(8) -0.0063(7) -0.0008(6) -0.0006(7) C1 0.0176(7) 0.0207(8) 0.0183(8) -0.0055(7) -0.0017(6) -0.0007(6) C2 0.0186(8) 0.0211(8) 0.0166(8) -0.0050(7) -0.0017(6) 0.0008(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 S1 O5 1.5166(16) . ? S1 C8 1.782(2) . ? S1 C9 1.788(2) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? Cl1 C2 1.727(2) . ? O4 N1 1.224(2) . ? O3 N1 1.226(2) . ? O2 C7 1.323(2) . ? O2 H1 0.94(4) . ? O1 C7 1.215(2) . ? N1 C4 1.472(2) . ? C4 C3 1.385(3) . ? C4 C5 1.386(3) . ? C6 C5 1.386(3) . ? C6 C1 1.397(3) . ? C6 H6 0.9500 . ? C3 C2 1.388(3) . ? C3 H3 0.9500 . ? C5 H5 0.9500 . ? C7 C1 1.502(3) . ? C1 C2 1.406(3) . ? 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 O5 S1 C8 106.03(10) . . ? O5 S1 C9 107.11(10) . . ? C8 S1 C9 97.91(10) . . ? S1 C8 H8A 109.5 . . ? S1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? S1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? S1 C9 H9A 109.5 . . ? S1 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? S1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C7 O2 H1 106(2) . . ? O4 N1 O3 123.56(18) . . ? O4 N1 C4 118.42(16) . . ? O3 N1 C4 118.03(17) . . ? C3 C4 C5 122.94(18) . . ? C3 C4 N1 117.94(17) . . ? C5 C4 N1 119.12(17) . . ? C5 C6 C1 122.26(18) . . ? C5 C6 H6 118.9 . . ? C1 C6 H6 118.9 . . ? C4 C3 C2 118.31(17) . . ? C4 C3 H3 120.8 . . ? C2 C3 H3 120.8 . . ? C4 C5 C6 117.41(18) . . ? C4 C5 H5 121.3 . . ? C6 C5 H5 121.3 . . ? O1 C7 O2 123.95(19) . . ? O1 C7 C1 123.93(18) . . ? O2 C7 C1 112.11(16) . . ? C6 C1 C2 117.94(18) . . ? C6 C1 C7 119.03(17) . . ? C2 C1 C7 123.04(17) . . ? C3 C2 C1 121.11(17) . . ? C3 C2 Cl1 116.01(14) . . ? C1 C2 Cl1 122.85(15) . . ? _diffrn_measured_fraction_theta_max 0.889 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.454 _refine_diff_density_min -0.491 _refine_diff_density_rms 0.091 #====END data_CNBA-Acetophenone _database_code_depnum_ccdc_archive 'CCDC 782722' #TrackingRef '- CEC-CIF.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 'acetophenone solvate of 2-chloro-4-nitrobenzoic acid' ; _chemical_name_common "'acetophenone solvate of 2-chloro-4-nitrobenzoic acid'" _chemical_melting_point ? _chemical_formula_moiety 'C7 H4 Cl N O4, C8 H8 O' _chemical_formula_sum 'C15 H12 Cl N O5' _chemical_formula_weight 321.71 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 5.8156(12) _cell_length_b 10.387(2) _cell_length_c 12.207(2) _cell_angle_alpha 83.67(3) _cell_angle_beta 77.63(3) _cell_angle_gamma 81.03(3) _cell_volume 709.2(2) _cell_formula_units_Z 2 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 2472 _cell_measurement_theta_min 2.5217 _cell_measurement_theta_max 30.8149 _exptl_crystal_description block _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.507 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 332 _exptl_absorpt_coefficient_mu 0.293 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9043 _exptl_absorpt_correction_T_max 0.9491 _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 10021 _diffrn_reflns_av_R_equivalents 0.0228 _diffrn_reflns_av_sigmaI/netI 0.0212 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.71 _diffrn_reflns_theta_max 28.28 _reflns_number_total 3477 _reflns_number_gt 3300 _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^)+(0.0625P)^2^+0.2612P] 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 3477 _refine_ls_number_parameters 204 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0432 _refine_ls_R_factor_gt 0.0400 _refine_ls_wR_factor_ref 0.1171 _refine_ls_wR_factor_gt 0.1076 _refine_ls_goodness_of_fit_ref 1.150 _refine_ls_restrained_S_all 1.150 _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 1.15380(6) 0.35605(3) 0.43986(3) 0.02388(12) Uani 1 1 d . . . O2 O 0.6536(2) 0.36420(11) 0.54491(10) 0.0261(2) Uani 1 1 d . . . O1 O 0.5254(2) 0.17054(11) 0.60204(10) 0.0287(3) Uani 1 1 d . . . O4 O 1.5313(2) 0.01145(12) 0.16170(10) 0.0305(3) Uani 1 1 d . . . O5 O -0.3641(2) 0.52341(12) 0.28334(10) 0.0334(3) Uani 1 1 d . . . O3 O 1.2712(2) -0.11209(13) 0.15087(11) 0.0382(3) Uani 1 1 d . . . C2 C 1.0625(2) 0.22173(13) 0.39837(12) 0.0180(3) Uani 1 1 d . . . C3 C 1.2239(2) 0.15455(14) 0.31599(12) 0.0197(3) Uani 1 1 d . . . H3 H 1.3749 0.1819 0.2862 0.024 Uiso 1 1 calc R . . C1 C 0.8419(2) 0.17949(13) 0.44432(11) 0.0184(3) Uani 1 1 d . . . C8 C -0.0400(3) 0.42380(13) 0.15706(11) 0.0193(3) Uani 1 1 d . . . N1 N 1.3339(2) -0.02330(12) 0.19049(11) 0.0243(3) Uani 1 1 d . . . C4 C 1.1606(2) 0.04692(14) 0.27808(12) 0.0199(3) Uani 1 1 d . . . C7 C 0.6579(2) 0.23761(14) 0.53901(12) 0.0204(3) Uani 1 1 d . . . C5 C 0.9434(3) 0.00349(14) 0.31843(12) 0.0215(3) Uani 1 1 d . . . H5 H 0.9024 -0.0692 0.2896 0.026 Uiso 1 1 calc R . . C9 C -0.1715(3) 0.32779(14) 0.14177(12) 0.0216(3) Uani 1 1 d . . . H9 H -0.3321 0.3295 0.1804 0.026 Uiso 1 1 calc R . . C14 C -0.1576(3) 0.52713(14) 0.23425(12) 0.0223(3) Uani 1 1 d . . . C13 C 0.1960(3) 0.41975(15) 0.10053(13) 0.0236(3) Uani 1 1 d . . . H13 H 0.2871 0.4843 0.1106 0.028 Uiso 1 1 calc R . . C6 C 0.7878(3) 0.07000(14) 0.40260(12) 0.0209(3) Uani 1 1 d . . . H6 H 0.6390 0.0403 0.4331 0.025 Uiso 1 1 calc R . . C11 C 0.1653(3) 0.22687(15) 0.01430(13) 0.0259(3) Uani 1 1 d . . . H11 H 0.2351 0.1600 -0.0345 0.031 Uiso 1 1 calc R . . C15 C -0.0240(3) 0.63312(15) 0.25021(13) 0.0280(3) Uani 1 1 d . . . H15A H -0.1283 0.6943 0.3009 0.042 Uiso 1 1 calc R . . H15B H 0.0304 0.6799 0.1773 0.042 Uiso 1 1 calc R . . H15C H 0.1135 0.5947 0.2829 0.042 Uiso 1 1 calc R . . C10 C -0.0695(3) 0.23025(15) 0.07063(13) 0.0255(3) Uani 1 1 d . . . H10 H -0.1603 0.1656 0.0604 0.031 Uiso 1 1 calc R . . C12 C 0.2985(3) 0.32148(16) 0.02937(13) 0.0263(3) Uani 1 1 d . . . H12 H 0.4594 0.3190 -0.0089 0.032 Uiso 1 1 calc R . . H1 H 0.541(5) 0.390(3) 0.605(2) 0.056(7) 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 0.0234(2) 0.02209(19) 0.0278(2) -0.00688(13) -0.00393(14) -0.00631(13) O2 0.0228(5) 0.0233(5) 0.0307(6) -0.0102(4) 0.0024(4) -0.0033(4) O1 0.0269(6) 0.0246(5) 0.0284(6) -0.0001(4) 0.0054(4) -0.0009(4) O4 0.0226(6) 0.0319(6) 0.0335(6) -0.0082(5) 0.0058(5) -0.0051(4) O5 0.0283(6) 0.0338(6) 0.0357(6) -0.0149(5) 0.0051(5) -0.0043(5) O3 0.0368(7) 0.0364(7) 0.0416(7) -0.0225(6) 0.0059(5) -0.0119(5) C2 0.0182(6) 0.0164(6) 0.0198(6) -0.0006(5) -0.0056(5) -0.0021(5) C3 0.0176(6) 0.0203(6) 0.0204(6) -0.0005(5) -0.0033(5) -0.0019(5) C1 0.0183(6) 0.0183(6) 0.0181(6) -0.0006(5) -0.0038(5) -0.0013(5) C8 0.0213(7) 0.0188(6) 0.0179(6) -0.0016(5) -0.0045(5) -0.0016(5) N1 0.0244(6) 0.0226(6) 0.0239(6) -0.0054(5) 0.0010(5) -0.0028(5) C4 0.0192(7) 0.0196(6) 0.0191(6) -0.0024(5) -0.0009(5) -0.0006(5) C7 0.0183(6) 0.0210(6) 0.0214(6) -0.0029(5) -0.0051(5) 0.0007(5) C5 0.0223(7) 0.0183(6) 0.0248(7) -0.0035(5) -0.0036(5) -0.0053(5) C9 0.0200(7) 0.0221(7) 0.0222(7) -0.0028(5) -0.0026(5) -0.0034(5) C14 0.0266(7) 0.0203(6) 0.0199(6) -0.0028(5) -0.0044(5) -0.0019(5) C13 0.0213(7) 0.0247(7) 0.0244(7) -0.0005(6) -0.0035(5) -0.0051(5) C6 0.0187(6) 0.0208(6) 0.0223(7) -0.0016(5) -0.0017(5) -0.0039(5) C11 0.0291(8) 0.0253(7) 0.0211(7) -0.0048(5) -0.0039(6) 0.0033(6) C15 0.0381(9) 0.0227(7) 0.0255(7) -0.0045(6) -0.0072(6) -0.0077(6) C10 0.0286(8) 0.0230(7) 0.0262(7) -0.0054(6) -0.0069(6) -0.0037(6) C12 0.0206(7) 0.0308(8) 0.0245(7) -0.0015(6) -0.0002(5) -0.0001(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 Cl1 C2 1.7284(14) . ? O2 C7 1.3210(18) . ? O2 H1 0.90(3) . ? O1 C7 1.2109(18) . ? O4 N1 1.2247(18) . ? O5 C14 1.2262(19) . ? O3 N1 1.2233(18) . ? C2 C3 1.388(2) . ? C2 C1 1.4021(19) . ? C3 C4 1.384(2) . ? C3 H3 0.9500 . ? C1 C6 1.400(2) . ? C1 C7 1.506(2) . ? C8 C13 1.394(2) . ? C8 C9 1.398(2) . ? C8 C14 1.492(2) . ? N1 C4 1.4737(19) . ? C4 C5 1.380(2) . ? C5 C6 1.384(2) . ? C5 H5 0.9500 . ? C9 C10 1.385(2) . ? C9 H9 0.9500 . ? C14 C15 1.494(2) . ? C13 C12 1.391(2) . ? C13 H13 0.9500 . ? C6 H6 0.9500 . ? C11 C10 1.388(2) . ? C11 C12 1.392(2) . ? C11 H11 0.9500 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C10 H10 0.9500 . ? C12 H12 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 C7 O2 H1 108.3(16) . . ? C3 C2 C1 120.65(13) . . ? C3 C2 Cl1 115.82(11) . . ? C1 C2 Cl1 123.52(11) . . ? C4 C3 C2 118.73(13) . . ? C4 C3 H3 120.6 . . ? C2 C3 H3 120.6 . . ? C6 C1 C2 118.03(13) . . ? C6 C1 C7 115.82(12) . . ? C2 C1 C7 126.09(13) . . ? C13 C8 C9 119.24(14) . . ? C13 C8 C14 122.17(13) . . ? C9 C8 C14 118.58(13) . . ? O3 N1 O4 124.21(13) . . ? O3 N1 C4 117.98(13) . . ? O4 N1 C4 117.80(13) . . ? C5 C4 C3 122.85(13) . . ? C5 C4 N1 119.08(13) . . ? C3 C4 N1 118.07(12) . . ? O1 C7 O2 124.53(14) . . ? O1 C7 C1 120.75(13) . . ? O2 C7 C1 114.71(12) . . ? C4 C5 C6 117.39(13) . . ? C4 C5 H5 121.3 . . ? C6 C5 H5 121.3 . . ? C10 C9 C8 120.48(14) . . ? C10 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? O5 C14 C8 118.91(13) . . ? O5 C14 C15 121.16(14) . . ? C8 C14 C15 119.93(13) . . ? C12 C13 C8 120.23(14) . . ? C12 C13 H13 119.9 . . ? C8 C13 H13 119.9 . . ? C5 C6 C1 122.31(13) . . ? C5 C6 H6 118.8 . . ? C1 C6 H6 118.8 . . ? C10 C11 C12 120.00(14) . . ? C10 C11 H11 120.0 . . ? C12 C11 H11 120.0 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C9 C10 C11 120.04(15) . . ? C9 C10 H10 120.0 . . ? C11 C10 H10 120.0 . . ? C13 C12 C11 120.00(14) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.375 _refine_diff_density_min -0.293 _refine_diff_density_rms 0.083 #====END data_CNBA-p-Xylene _database_code_depnum_ccdc_archive 'CCDC 782723' #TrackingRef '- CEC-CIF.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 'p-xylene solvate of 2-chloro-4-nitrobenzoic acid' ; _chemical_name_common "'p-xylene solvate of 2-chloro-4-nitrobenzoic acid'" _chemical_melting_point ? _chemical_formula_moiety 'C8 H10, 2(C7 H4 Cl N O4)' _chemical_formula_sum 'C22 H18 Cl2 N2 O8' _chemical_formula_weight 509.28 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 monoclinic _symmetry_space_group_name_H-M 'P 21/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 10.790(2) _cell_length_b 11.767(2) _cell_length_c 8.9666(18) _cell_angle_alpha 90.00 _cell_angle_beta 90.71(3) _cell_angle_gamma 90.00 _cell_volume 1138.4(4) _cell_formula_units_Z 2 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 3143 _cell_measurement_theta_min 2.5613 _cell_measurement_theta_max 30.9524 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.486 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 524 _exptl_absorpt_coefficient_mu 0.337 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8658 _exptl_absorpt_correction_T_max 0.9568 _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 8254 _diffrn_reflns_av_R_equivalents 0.0335 _diffrn_reflns_av_sigmaI/netI 0.0361 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 28.28 _reflns_number_total 2807 _reflns_number_gt 2553 _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^)+(0.0898P)^2^+0.7097P] 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 2807 _refine_ls_number_parameters 159 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0749 _refine_ls_R_factor_gt 0.0669 _refine_ls_wR_factor_ref 0.1861 _refine_ls_wR_factor_gt 0.1740 _refine_ls_goodness_of_fit_ref 1.196 _refine_ls_restrained_S_all 1.196 _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 0.32901(6) 1.21605(5) 0.13279(7) 0.0349(2) Uani 1 1 d . . . O3 O 0.22368(18) 0.84516(16) -0.3389(2) 0.0359(4) Uani 1 1 d . . . N1 N 0.24785(19) 0.94167(18) -0.2957(2) 0.0283(4) Uani 1 1 d . . . O1 O 0.47520(17) 1.08519(15) 0.3530(2) 0.0318(4) Uani 1 1 d . . . O2 O 0.42752(18) 0.90159(16) 0.3777(2) 0.0333(4) Uani 1 1 d . . . C6 C 0.3759(2) 0.8781(2) 0.0822(3) 0.0274(5) Uani 1 1 d . . . H6 H 0.4047 0.8145 0.1380 0.033 Uiso 1 1 calc R . . C2 C 0.3354(2) 1.0791(2) 0.0644(3) 0.0256(5) Uani 1 1 d . . . C7 C 0.4305(2) 0.9964(2) 0.3031(3) 0.0262(5) Uani 1 1 d . . . O4 O 0.2397(2) 1.02688(17) -0.3738(2) 0.0388(5) Uani 1 1 d . . . C4 C 0.2919(2) 0.9558(2) -0.1402(3) 0.0255(5) Uani 1 1 d . . . C1 C 0.3792(2) 0.9863(2) 0.1477(3) 0.0251(5) Uani 1 1 d . . . C3 C 0.2917(2) 1.0642(2) -0.0810(3) 0.0264(5) Uani 1 1 d . . . H3 H 0.2624 1.1269 -0.1380 0.032 Uiso 1 1 calc R . . C5 C 0.3319(2) 0.8618(2) -0.0615(3) 0.0276(5) Uani 1 1 d . . . H5 H 0.3292 0.7881 -0.1047 0.033 Uiso 1 1 calc R . . C9 C 0.0178(3) 0.0768(3) 0.1132(4) 0.0440(7) Uani 1 1 d . . . H9 H 0.0297 0.1311 0.1904 0.053 Uiso 1 1 calc R . . C10 C -0.0186(3) 0.1136(3) -0.0281(4) 0.0436(7) Uani 1 1 d . . . H10 H -0.0310 0.1924 -0.0456 0.052 Uiso 1 1 calc R . . C8 C 0.0369(2) -0.0372(3) 0.1438(3) 0.0419(7) Uani 1 1 d . . . C11 C 0.0747(3) -0.0784(4) 0.2980(4) 0.0618(11) Uani 1 1 d . . . H11A H 0.0010 -0.1032 0.3519 0.093 Uiso 1 1 calc R . . H11B H 0.1151 -0.0163 0.3530 0.093 Uiso 1 1 calc R . . H11C H 0.1325 -0.1422 0.2890 0.093 Uiso 1 1 calc R . . H1 H 0.455(5) 0.913(4) 0.468(6) 0.090(16) 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 0.0469(4) 0.0242(3) 0.0335(4) -0.0041(2) -0.0021(3) 0.0013(2) O3 0.0432(10) 0.0318(10) 0.0325(10) -0.0064(8) -0.0062(8) -0.0022(8) N1 0.0288(10) 0.0304(10) 0.0258(10) -0.0030(8) 0.0004(8) 0.0011(8) O1 0.0405(10) 0.0308(9) 0.0239(9) -0.0017(7) -0.0025(7) -0.0066(7) O2 0.0436(10) 0.0294(9) 0.0266(9) 0.0025(7) -0.0058(8) -0.0042(7) C6 0.0277(11) 0.0269(11) 0.0275(12) -0.0004(9) 0.0016(9) -0.0002(9) C2 0.0255(11) 0.0245(11) 0.0269(12) -0.0013(9) 0.0022(9) -0.0006(8) C7 0.0245(10) 0.0271(11) 0.0272(11) -0.0004(9) 0.0026(9) -0.0017(8) O4 0.0531(12) 0.0338(10) 0.0291(9) 0.0036(8) -0.0078(8) 0.0003(8) C4 0.0233(10) 0.0292(12) 0.0239(11) -0.0029(9) 0.0016(9) -0.0005(8) C1 0.0237(10) 0.0275(11) 0.0242(11) -0.0002(9) 0.0023(9) -0.0026(8) C3 0.0266(11) 0.0267(11) 0.0261(11) 0.0011(9) 0.0013(9) 0.0002(8) C5 0.0287(11) 0.0246(11) 0.0296(12) -0.0020(9) 0.0004(9) -0.0008(9) C9 0.0301(13) 0.0590(19) 0.0429(16) -0.0108(14) 0.0046(12) 0.0001(12) C10 0.0334(13) 0.0466(16) 0.0510(18) 0.0059(14) 0.0077(12) 0.0064(12) C8 0.0237(12) 0.068(2) 0.0345(14) 0.0061(13) 0.0023(10) 0.0051(12) C11 0.0453(17) 0.101(3) 0.0392(17) 0.0147(19) 0.0021(14) 0.0170(18) _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 1.726(2) . ? O3 N1 1.227(3) . ? N1 O4 1.226(3) . ? N1 C4 1.477(3) . ? O1 C7 1.233(3) . ? O2 C7 1.301(3) . ? O2 H1 0.87(5) . ? C6 C5 1.381(3) . ? C6 C1 1.403(3) . ? C6 H6 0.9500 . ? C2 C3 1.392(3) . ? C2 C1 1.401(3) . ? C7 C1 1.498(3) . ? C4 C5 1.379(3) . ? C4 C3 1.382(3) . ? C3 H3 0.9500 . ? C5 H5 0.9500 . ? C9 C8 1.384(5) . ? C9 C10 1.391(5) . ? C9 H9 0.9500 . ? C10 C8 1.384(5) 3 ? C10 H10 0.9500 . ? C8 C10 1.384(5) 3 ? C8 C11 1.517(4) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 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 O4 N1 O3 124.3(2) . . ? O4 N1 C4 117.9(2) . . ? O3 N1 C4 117.8(2) . . ? C7 O2 H1 110(3) . . ? C5 C6 C1 121.5(2) . . ? C5 C6 H6 119.2 . . ? C1 C6 H6 119.2 . . ? C3 C2 C1 120.6(2) . . ? C3 C2 Cl1 115.85(18) . . ? C1 C2 Cl1 123.50(19) . . ? O1 C7 O2 123.5(2) . . ? O1 C7 C1 122.9(2) . . ? O2 C7 C1 113.5(2) . . ? C5 C4 C3 123.1(2) . . ? C5 C4 N1 119.2(2) . . ? C3 C4 N1 117.7(2) . . ? C2 C1 C6 118.5(2) . . ? C2 C1 C7 123.6(2) . . ? C6 C1 C7 117.9(2) . . ? C4 C3 C2 118.3(2) . . ? C4 C3 H3 120.9 . . ? C2 C3 H3 120.9 . . ? C4 C5 C6 117.9(2) . . ? C4 C5 H5 121.0 . . ? C6 C5 H5 121.0 . . ? C8 C9 C10 121.5(3) . . ? C8 C9 H9 119.3 . . ? C10 C9 H9 119.3 . . ? C8 C10 C9 121.1(3) 3 . ? C8 C10 H10 119.5 3 . ? C9 C10 H10 119.5 . . ? C9 C8 C10 117.5(3) . 3 ? C9 C8 C11 121.9(3) . . ? C10 C8 C11 120.7(3) 3 . ? C8 C11 H11A 109.5 . . ? C8 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C8 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.563 _refine_diff_density_min -0.507 _refine_diff_density_rms 0.121 #====END data_CNBA-Mesitylene _database_code_depnum_ccdc_archive 'CCDC 782724' #TrackingRef '- CEC-CIF.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 'mesitylene solvate of 2-chloro-4-nitrobenzoic acid' ; _chemical_name_common "'mesitylene solvate of 2-chloro-4-nitrobenzoic acid'" _chemical_formula_moiety 'C9 H12, 2(C7 H4 Cl N O4)' _chemical_formula_sum 'C23 H20 Cl2 N2 O8' _chemical_formula_weight 523.31 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' 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 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' 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 23.088(5) _cell_length_b 12.018(2) _cell_length_c 8.9206(18) _cell_angle_alpha 90.00 _cell_angle_beta 110.29(3) _cell_angle_gamma 90.00 _cell_volume 2321.7(8) _cell_formula_units_Z 4 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 3161 _cell_measurement_theta_min 1.8808 _cell_measurement_theta_max 31.0496 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.497 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1080 _exptl_absorpt_coefficient_mu 0.333 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8981 _exptl_absorpt_correction_T_max 0.9505 _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 9061 _diffrn_reflns_av_R_equivalents 0.0302 _diffrn_reflns_av_sigmaI/netI 0.0271 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 28.28 _reflns_number_total 2867 _reflns_number_gt 2640 _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^)+(0.0759P)^2^+1.8088P] 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 2867 _refine_ls_number_parameters 166 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0594 _refine_ls_R_factor_gt 0.0520 _refine_ls_wR_factor_ref 0.1511 _refine_ls_wR_factor_gt 0.1381 _refine_ls_goodness_of_fit_ref 1.183 _refine_ls_restrained_S_all 1.183 _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 Cl1 Cl 0.32865(3) 0.96295(4) 0.20251(6) 0.03534(18) Uani 1 1 d . . . O2 O 0.28746(7) 0.65136(12) 0.41171(18) 0.0322(3) Uani 1 1 d . . . O3 O 0.38550(7) 0.60190(12) -0.22015(18) 0.0330(3) Uani 1 1 d . . . C1 C 0.31053(8) 0.73600(15) 0.2029(2) 0.0237(4) Uani 1 1 d . . . O1 O 0.26131(7) 0.83053(12) 0.36349(18) 0.0321(3) Uani 1 1 d . . . N1 N 0.37663(8) 0.69613(14) -0.1812(2) 0.0276(3) Uani 1 1 d . . . O4 O 0.38363(9) 0.78057(13) -0.2501(2) 0.0426(4) Uani 1 1 d . . . C2 C 0.32956(9) 0.82840(15) 0.1359(2) 0.0252(4) Uani 1 1 d . . . C5 C 0.33738(8) 0.61523(15) 0.0186(2) 0.0256(4) Uani 1 1 d . . . H5 H 0.3405 0.5431 -0.0215 0.031 Uiso 1 1 calc R . . C7 C 0.28446(8) 0.74505(15) 0.3344(2) 0.0247(4) Uani 1 1 d . . . C4 C 0.35484(8) 0.70887(15) -0.0447(2) 0.0247(4) Uani 1 1 d . . . C3 C 0.35213(8) 0.81492(15) 0.0110(2) 0.0256(4) Uani 1 1 d . . . H3 H 0.3653 0.8772 -0.0345 0.031 Uiso 1 1 calc R . . C6 C 0.31517(8) 0.63036(15) 0.1429(2) 0.0248(4) Uani 1 1 d . . . H6 H 0.3028 0.5673 0.1884 0.030 Uiso 1 1 calc R . . C11 C 0.5000 0.6500(2) 0.2500 0.0309(6) Uani 1 2 d S . . H11 H 0.5000 0.5710 0.2500 0.037 Uiso 1 2 calc SR . . C8 C 0.48050(8) 0.70630(18) 0.3606(2) 0.0308(4) Uani 1 1 d . . . C9 C 0.48074(10) 0.82203(19) 0.3583(3) 0.0364(5) Uani 1 1 d . . . H9 H 0.4674 0.8616 0.4326 0.044 Uiso 1 1 calc R . . C12 C 0.45997(10) 0.6448(2) 0.4810(3) 0.0390(5) Uani 1 1 d . . . H12A H 0.4962 0.6254 0.5740 0.058 Uiso 1 1 calc R . . H12B H 0.4382 0.5767 0.4322 0.058 Uiso 1 1 calc R . . H12C H 0.4323 0.6923 0.5148 0.058 Uiso 1 1 calc R . . C13 C 0.5000 1.0067(3) 0.2500 0.0736(14) Uani 1 2 d S . . H13A H 0.4678 1.0339 0.2891 0.110 Uiso 0.50 1 calc PR . . H13B H 0.4918 1.0339 0.1410 0.110 Uiso 0.50 1 calc PR . . H13C H 0.5404 1.0339 0.3199 0.110 Uiso 0.50 1 calc PR . . C10 C 0.5000 0.8815(3) 0.2500 0.0421(7) Uani 1 2 d S . . H1 H 0.2731(15) 0.665(2) 0.489(4) 0.058(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 Cl1 0.0501(3) 0.0216(3) 0.0365(3) -0.00406(17) 0.0178(2) -0.00007(18) O2 0.0419(8) 0.0276(7) 0.0334(8) 0.0032(6) 0.0212(7) 0.0042(6) O3 0.0391(8) 0.0290(7) 0.0342(8) -0.0039(6) 0.0170(6) 0.0026(6) C1 0.0221(8) 0.0259(9) 0.0199(8) 0.0001(6) 0.0032(6) 0.0020(6) O1 0.0400(8) 0.0293(7) 0.0295(7) 0.0011(5) 0.0151(6) 0.0075(6) N1 0.0287(8) 0.0270(8) 0.0280(8) -0.0012(6) 0.0108(6) -0.0004(6) O4 0.0648(11) 0.0306(8) 0.0436(9) 0.0037(7) 0.0331(8) -0.0030(7) C2 0.0264(8) 0.0223(8) 0.0237(9) -0.0007(6) 0.0046(7) 0.0016(6) C5 0.0254(8) 0.0226(8) 0.0278(9) -0.0007(7) 0.0079(7) 0.0019(6) C7 0.0232(8) 0.0269(9) 0.0211(8) -0.0010(7) 0.0041(7) 0.0004(7) C4 0.0226(8) 0.0271(9) 0.0235(9) -0.0003(7) 0.0070(7) 0.0022(7) C3 0.0262(8) 0.0239(8) 0.0254(9) 0.0014(7) 0.0072(7) -0.0002(6) C6 0.0243(8) 0.0231(8) 0.0252(9) 0.0007(7) 0.0063(7) 0.0002(6) C11 0.0273(12) 0.0328(14) 0.0294(14) 0.000 0.0060(11) 0.000 C8 0.0243(9) 0.0390(11) 0.0258(9) 0.0007(8) 0.0046(7) 0.0010(7) C9 0.0354(11) 0.0400(12) 0.0305(11) -0.0029(8) 0.0072(9) 0.0046(8) C12 0.0330(10) 0.0517(13) 0.0323(11) 0.0027(9) 0.0114(9) -0.0003(9) C13 0.125(4) 0.0339(19) 0.064(3) 0.000 0.036(3) 0.000 C10 0.0487(18) 0.0373(16) 0.0336(16) 0.000 0.0059(14) 0.000 _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 1.7256(19) . ? O2 C7 1.310(2) . ? O2 H1 0.88(3) . ? O3 N1 1.223(2) . ? C1 C6 1.397(3) . ? C1 C2 1.402(3) . ? C1 C7 1.496(3) . ? O1 C7 1.227(2) . ? N1 O4 1.226(2) . ? N1 C4 1.477(2) . ? C2 C3 1.393(3) . ? C5 C4 1.381(3) . ? C5 C6 1.385(3) . ? C5 H5 0.9500 . ? C4 C3 1.377(3) . ? C3 H3 0.9500 . ? C6 H6 0.9500 . ? C11 C8 1.394(3) 2_655 ? C11 C8 1.394(3) . ? C11 H11 0.9500 . ? C8 C9 1.391(3) . ? C8 C12 1.509(3) . ? C9 C10 1.392(3) . ? C9 H9 0.9500 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C10 1.506(5) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C10 C9 1.392(3) 2_655 ? 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 C7 O2 H1 106(2) . . ? C6 C1 C2 118.63(17) . . ? C6 C1 C7 118.16(16) . . ? C2 C1 C7 123.20(16) . . ? O3 N1 O4 124.05(17) . . ? O3 N1 C4 117.95(16) . . ? O4 N1 C4 117.99(16) . . ? C3 C2 C1 120.56(17) . . ? C3 C2 Cl1 115.92(14) . . ? C1 C2 Cl1 123.50(15) . . ? C4 C5 C6 117.53(17) . . ? C4 C5 H5 121.2 . . ? C6 C5 H5 121.2 . . ? O1 C7 O2 123.75(18) . . ? O1 C7 C1 123.38(17) . . ? O2 C7 C1 112.84(15) . . ? C3 C4 C5 123.39(18) . . ? C3 C4 N1 117.66(16) . . ? C5 C4 N1 118.95(16) . . ? C4 C3 C2 118.20(17) . . ? C4 C3 H3 120.9 . . ? C2 C3 H3 120.9 . . ? C5 C6 C1 121.68(17) . . ? C5 C6 H6 119.2 . . ? C1 C6 H6 119.2 . . ? C8 C11 C8 121.9(3) 2_655 . ? C8 C11 H11 119.0 2_655 . ? C8 C11 H11 119.0 . . ? C9 C8 C11 118.1(2) . . ? C9 C8 C12 120.3(2) . . ? C11 C8 C12 121.6(2) . . ? C8 C9 C10 121.8(2) . . ? C8 C9 H9 119.1 . . ? C10 C9 H9 119.1 . . ? C8 C12 H12A 109.5 . . ? C8 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C8 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C10 C13 H13A 109.5 . . ? C10 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C10 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C9 C10 C9 118.3(3) . 2_655 ? C9 C10 C13 120.86(15) . . ? C9 C10 C13 120.86(15) 2_655 . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.416 _refine_diff_density_min -0.363 _refine_diff_density_rms 0.101 #====END