############################################################################## # # # This CIF contains the data in a paper accepted for publication in # # Acta Crystallographica Section E. It conforms to the requirements of # # Notes for Authors for Acta Crystallographica Section E, and has been # # peer reviewed under the auspices of the IUCr Commission on Journals. # # # # Full details of the Crystallographic Information File format # # are given in the paper "The Crystallographic Information File (CIF): # # a New Standard Archive File for Crystallography" by S. R. Hall, F. H. # # Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685]. # # # # The current version of the core CIF dictionary is obtainable from # # ftp://ftp.iucr.org/pub/cif_core.dic. # # # # Software is freely available for graphical display of the structure(s) # # in this CIF. For information consult the CIF software page # # http://www.iucr.org/resources/cif/software. # # # # This file may be used for bona fide research purposes within the # # scientific community so long as proper attribution is given to the journal # # article from which it was obtained. # # # ############################################################################## data_I _audit_creation_method SHELXL-97 _chemical_name_systematic ; (2-Chloro-3,5-dinitrophenyl)(piperidin-1-yl)methanone ; _chemical_name_common ? _chemical_formula_moiety 'C12 H12 Cl N3 O5' _chemical_formula_sum 'C12 H12 Cl N3 O5' _chemical_formula_iupac 'C12 H12 Cl N3 O5' _chemical_formula_weight 313.70 _chemical_melting_point ? _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, -y, z+1/2' 3 'x+1/2, -y+1/2, -z' 4 '-x, y+1/2, -z+1/2' 5 '-x, -y, -z' 6 'x-1/2, y, -z-1/2' 7 '-x-1/2, y-1/2, z' 8 'x, -y-1/2, z-1/2' _cell_length_a 10.7864(3) _cell_length_b 11.1264(3) _cell_length_c 21.9775(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2637.60(11) _cell_formula_units_Z 8 _cell_measurement_reflns_used 3316 _cell_measurement_theta_min 3.2116 _cell_measurement_theta_max 29.0546 _cell_measurement_temperature 150.0 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.20 _exptl_crystal_density_diffrn 1.580 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1296 _exptl_absorpt_coefficient_mu 0.317 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; (CrysAlisPro; Oxford Diffraction, 2006) ; _exptl_absorpt_correction_T_min 0.97869 _exptl_absorpt_correction_T_max 1.0 _exptl_special_details ; ; _diffrn_ambient_temperature 150.0 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur Eos' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.0874 _diffrn_reflns_number 6722 _diffrn_reflns_av_R_equivalents 0.0210 _diffrn_reflns_av_sigmaI/netI 0.0308 _diffrn_reflns_theta_min 3.22 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 15 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _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^ > \s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _reflns_number_total 2696 _reflns_number_gt 2240 _reflns_threshold_expression I>2\s(I) _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_R_factor_all 0.0437 _refine_ls_R_factor_gt 0.0331 _refine_ls_wR_factor_gt 0.0711 _refine_ls_wR_factor_ref 0.0765 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _refine_ls_number_reflns 2696 _refine_ls_number_parameters 238 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment refall _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; calc w=1/[\s^2^(Fo^2^)+(0.0283P)^2^+0.9862P] where P=(Fo^2^+2Fc^2^)/3 ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.250 _refine_diff_density_min -0.238 _refine_ls_extinction_method none _refine_ls_extinction_coef ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' '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' _computing_data_collection ; CrysAlisPro (Oxford Diffraction, 2006) ; _computing_cell_refinement ; CrysAlisPro ; _computing_data_reduction ; CrysAlisPro (Oxford Diffraction, 2006) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ; OLEX2 (Dolomanov et al., 2009) ; _computing_publication_material ; OLEX2 (Dolomanov et al., 2009) ; loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_disorder_assembly _atom_site_disorder_group Cl Cl1 0.14710(4) 0.51437(4) 0.126198(18) 0.02618(12) Uani d . 1 1 . . O O1 0.28382(11) 0.39665(10) 0.03083(6) 0.0308(3) Uani d . 1 1 . . O O2 0.37259(10) 0.52238(11) -0.03080(6) 0.0297(3) Uani d . 1 1 . . O O3 0.06436(13) 0.74355(12) -0.14870(6) 0.0376(3) Uani d . 1 1 . . O O4 -0.09872(13) 0.81129(12) -0.10265(6) 0.0409(4) Uani d . 1 1 . . O O5 -0.18116(11) 0.60708(11) 0.10878(6) 0.0331(3) Uani d . 1 1 . . N N1 0.28706(12) 0.49108(12) 0.00224(6) 0.0219(3) Uani d . 1 1 . . N N2 -0.00012(14) 0.75653(13) -0.10356(7) 0.0269(3) Uani d . 1 1 . . N N3 -0.05433(13) 0.73621(12) 0.15851(6) 0.0238(3) Uani d . 1 1 . . C C1 0.10865(14) 0.58412(14) 0.05898(7) 0.0179(3) Uani d . 1 1 . . C C2 0.17880(14) 0.57192(13) 0.00600(7) 0.0178(3) Uani d . 1 1 . . C C3 0.14762(15) 0.63140(14) -0.04708(7) 0.0188(3) Uani d . 1 1 . . H H3 0.1955(17) 0.6182(15) -0.0830(8) 0.028(5) Uiso d . 1 1 . . C C4 0.04113(15) 0.69969(13) -0.04645(7) 0.0191(3) Uani d . 1 1 . . C C5 -0.03125(16) 0.71333(14) 0.00470(7) 0.0204(4) Uani d . 1 1 . . H H5 -0.1055(16) 0.7566(15) 0.0036(7) 0.018(4) Uiso d . 1 1 . . C C6 0.00352(14) 0.65690(13) 0.05846(7) 0.0177(3) Uani d . 1 1 . . C C7 -0.08451(15) 0.66492(14) 0.11200(7) 0.0207(3) Uani d . 1 1 . . C C8 0.05941(16) 0.80784(16) 0.16249(9) 0.0274(4) Uani d . 1 1 . . H H8A 0.1068(18) 0.7963(17) 0.1263(9) 0.034(5) Uiso d . 1 1 . . H H8B 0.1111(17) 0.7754(16) 0.1984(9) 0.032(5) Uiso d . 1 1 . . C C9 0.02738(18) 0.93938(16) 0.17196(8) 0.0274(4) Uani d . 1 1 . . H H9A -0.0143(18) 0.9693(16) 0.1353(9) 0.031(5) Uiso d . 1 1 . . H H9B 0.1038(18) 0.9841(16) 0.1769(8) 0.029(5) Uiso d . 1 1 . . C C10 -0.05450(17) 0.95620(17) 0.22745(8) 0.0274(4) Uani d . 1 1 . . H H10A -0.0069(16) 0.9325(15) 0.2639(8) 0.025(5) Uiso d . 1 1 . . H H10B -0.0785(17) 1.0388(17) 0.2320(8) 0.033(5) Uiso d . 1 1 . . C C11 -0.16990(17) 0.87786(17) 0.22253(9) 0.0306(4) Uani d . 1 1 . . H H11A -0.2230(19) 0.9067(18) 0.1888(9) 0.040(6) Uiso d . 1 1 . . H H11B -0.2193(18) 0.8836(16) 0.2593(10) 0.041(6) Uiso d . 1 1 . . C C12 -0.13634(17) 0.74677(16) 0.21155(8) 0.0269(4) Uani d . 1 1 . . H H12A -0.2103(16) 0.7001(15) 0.2041(8) 0.022(4) Uiso d . 1 1 . . H H12B -0.0908(17) 0.7123(15) 0.2473(9) 0.028(5) Uiso d . 1 1 . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Cl1 0.0277(2) 0.0334(2) 0.0174(2) 0.00122(18) -0.00259(17) 0.00550(16) O1 0.0322(7) 0.0251(6) 0.0350(7) 0.0091(6) -0.0015(6) 0.0029(6) O2 0.0189(6) 0.0370(7) 0.0332(7) -0.0013(5) 0.0053(5) -0.0070(6) O3 0.0446(8) 0.0466(8) 0.0216(7) -0.0021(7) -0.0007(6) 0.0093(6) O4 0.0399(8) 0.0395(8) 0.0434(8) 0.0123(7) -0.0068(7) 0.0168(7) O5 0.0250(6) 0.0402(7) 0.0341(7) -0.0139(6) 0.0082(6) -0.0182(6) N1 0.0188(7) 0.0246(7) 0.0222(7) 0.0011(6) -0.0029(6) -0.0045(6) N2 0.0329(8) 0.0232(7) 0.0246(8) -0.0050(7) -0.0055(7) 0.0064(6) N3 0.0220(7) 0.0285(7) 0.0209(7) -0.0096(6) 0.0061(6) -0.0079(6) C1 0.0199(7) 0.0175(8) 0.0162(7) -0.0048(7) -0.0022(7) 0.0008(6) C2 0.0172(7) 0.0166(8) 0.0198(8) -0.0012(7) -0.0015(6) -0.0035(6) C3 0.0215(8) 0.0191(8) 0.0159(8) -0.0049(7) 0.0011(7) -0.0026(6) C4 0.0244(8) 0.0141(7) 0.0187(8) -0.0030(7) -0.0036(7) 0.0014(6) C5 0.0203(8) 0.0154(8) 0.0256(9) 0.0010(7) -0.0010(7) -0.0022(7) C6 0.0193(7) 0.0151(7) 0.0186(8) -0.0038(6) 0.0001(7) -0.0048(6) C7 0.0205(8) 0.0189(8) 0.0228(9) -0.0007(7) 0.0018(7) -0.0032(7) C8 0.0225(9) 0.0332(10) 0.0266(10) -0.0106(8) 0.0062(8) -0.0110(8) C9 0.0303(10) 0.0295(10) 0.0224(9) -0.0119(8) 0.0016(8) -0.0023(7) C10 0.0308(9) 0.0256(9) 0.0258(9) -0.0027(8) 0.0018(8) -0.0077(8) C11 0.0261(9) 0.0381(11) 0.0277(10) -0.0018(8) 0.0076(8) -0.0098(8) C12 0.0272(9) 0.0322(9) 0.0212(9) -0.0100(8) 0.0084(8) -0.0058(8) _geom_special_details ; All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Cl1 C1 . 1.7196(16) ? O1 N1 . 1.2247(17) ? O2 N1 . 1.2246(17) ? O3 N2 . 1.2200(19) ? O4 N2 . 1.2260(19) ? O5 C7 . 1.2273(19) ? N1 C2 . 1.476(2) ? N2 C4 . 1.474(2) ? N3 C7 . 1.334(2) ? N3 C8 . 1.466(2) ? N3 C12 . 1.468(2) ? C1 C2 . 1.395(2) ? C1 C6 . 1.394(2) ? C2 C3 . 1.383(2) ? C3 H3 . 0.954(18) ? C3 C4 . 1.377(2) ? C4 C5 . 1.377(2) ? C5 H5 . 0.935(17) ? C5 C6 . 1.389(2) ? C6 C7 . 1.515(2) ? C8 H8A . 0.95(2) ? C8 H8B . 1.032(19) ? C8 C9 . 1.518(3) ? C9 H9A . 0.98(2) ? C9 H9B . 0.97(2) ? C9 C10 . 1.517(2) ? C10 H10A . 0.987(18) ? C10 H10B . 0.960(19) ? C10 C11 . 1.523(2) ? C11 H11A . 0.99(2) ? C11 H11B . 0.97(2) ? C11 C12 . 1.522(3) ? C12 H12A . 0.966(17) ? C12 H12B . 1.004(19) ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O1 N1 C2 . . 118.12(13) ? O2 N1 O1 . . 124.73(14) ? O2 N1 C2 . . 117.11(13) ? O3 N2 O4 . . 124.53(15) ? O3 N2 C4 . . 118.00(14) ? O4 N2 C4 . . 117.45(15) ? O5 C7 N3 . . 124.28(15) ? O5 C7 C6 . . 117.18(14) ? N3 C7 C6 . . 118.51(13) ? N3 C8 H8A . . 109.0(11) ? N3 C8 H8B . . 107.9(10) ? N3 C8 C9 . . 109.99(15) ? N3 C12 C11 . . 110.24(15) ? N3 C12 H12A . . 108.7(10) ? N3 C12 H12B . . 107.2(10) ? C1 C2 N1 . . 122.34(14) ? C1 C6 C7 . . 122.55(14) ? C2 C1 Cl1 . . 122.84(12) ? C2 C3 H3 . . 119.5(11) ? C3 C2 N1 . . 115.90(14) ? C3 C2 C1 . . 121.70(14) ? C3 C4 N2 . . 118.68(14) ? C4 C3 C2 . . 117.30(15) ? C4 C3 H3 . . 122.9(11) ? C4 C5 H5 . . 121.5(10) ? C4 C5 C6 . . 119.43(15) ? C5 C4 N2 . . 118.47(14) ? C5 C4 C3 . . 122.80(15) ? C5 C6 C1 . . 119.29(14) ? C5 C6 C7 . . 117.69(14) ? C6 C1 Cl1 . . 117.75(12) ? C6 C1 C2 . . 119.41(14) ? C6 C5 H5 . . 119.0(10) ? C7 N3 C8 . . 124.97(14) ? C7 N3 C12 . . 120.59(13) ? C8 N3 C12 . . 114.43(13) ? C8 C9 H9A . . 108.6(11) ? C8 C9 H9B . . 108.5(10) ? H8A C8 H8B . . 107.6(15) ? C9 C8 H8A . . 111.5(12) ? C9 C8 H8B . . 110.8(10) ? C9 C10 H10A . . 108.5(10) ? C9 C10 H10B . . 111.1(11) ? C9 C10 C11 . . 110.37(15) ? H9A C9 H9B . . 107.9(15) ? C10 C9 C8 . . 111.20(15) ? C10 C9 H9A . . 110.6(11) ? C10 C9 H9B . . 110.0(11) ? C10 C11 H11A . . 109.9(12) ? C10 C11 H11B . . 110.6(11) ? H10A C10 H10B . . 108.1(15) ? C11 C10 H10A . . 109.2(10) ? C11 C10 H10B . . 109.5(11) ? C11 C12 H12A . . 110.2(10) ? C11 C12 H12B . . 111.0(10) ? H11A C11 H11B . . 106.6(16) ? C12 C11 C10 . . 111.42(15) ? C12 C11 H11A . . 109.2(12) ? C12 C11 H11B . . 109.0(11) ? H12A C12 H12B . . 109.3(14) ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag Cl1 C1 C2 N1 . . . . 4.4(2) ? Cl1 C1 C2 C3 . . . . -178.34(12) ? Cl1 C1 C6 C5 . . . . -179.12(12) ? Cl1 C1 C6 C7 . . . . -7.17(19) ? O1 N1 C2 C1 . . . . 34.7(2) ? O1 N1 C2 C3 . . . . -142.65(15) ? O2 N1 C2 C1 . . . . -147.16(15) ? O2 N1 C2 C3 . . . . 35.45(19) ? O3 N2 C4 C3 . . . . -2.2(2) ? O3 N2 C4 C5 . . . . -179.72(14) ? O4 N2 C4 C3 . . . . 176.04(14) ? O4 N2 C4 C5 . . . . -1.4(2) ? N1 C2 C3 C4 . . . . 174.76(13) ? N2 C4 C5 C6 . . . . 177.67(14) ? N3 C8 C9 C10 . . . . 55.5(2) ? C1 C2 C3 C4 . . . . -2.6(2) ? C1 C6 C7 O5 . . . . -100.86(19) ? C1 C6 C7 N3 . . . . 81.0(2) ? C2 C1 C6 C5 . . . . 1.7(2) ? C2 C1 C6 C7 . . . . 173.67(14) ? C2 C3 C4 N2 . . . . -175.24(14) ? C2 C3 C4 C5 . . . . 2.1(2) ? C3 C4 C5 C6 . . . . 0.3(2) ? C4 C5 C6 C1 . . . . -2.2(2) ? C4 C5 C6 C7 . . . . -174.59(14) ? C5 C6 C7 O5 . . . . 71.21(19) ? C5 C6 C7 N3 . . . . -106.95(18) ? C6 C1 C2 N1 . . . . -176.46(13) ? C6 C1 C2 C3 . . . . 0.8(2) ? C7 N3 C8 C9 . . . . 123.65(18) ? C7 N3 C12 C11 . . . . -124.47(17) ? C8 N3 C7 O5 . . . . -178.63(17) ? C8 N3 C7 C6 . . . . -0.6(2) ? C8 N3 C12 C11 . . . . 56.3(2) ? C8 C9 C10 C11 . . . . -55.0(2) ? C9 C10 C11 C12 . . . . 54.1(2) ? C10 C11 C12 N3 . . . . -53.7(2) ? C12 N3 C7 O5 . . . . 2.2(3) ? C12 N3 C7 C6 . . . . -179.80(15) ? C12 N3 C8 C9 . . . . -57.1(2) ? data_global _journal_date_recd_electronic 2011-03-14 _journal_date_accepted 2011-03-28 _journal_name_full 'Acta Crystallographica, Section E' _journal_year 2011 _journal_volume 67 _journal_issue 5 _journal_page_first o1066 _journal_page_last o1066 _journal_paper_category QO _journal_coeditor_code BT5492 _publ_contact_author_name 'Yu, Luo-ting' _publ_contact_author_address ; State Key Laboratory of Biotherapy and Cancer Center, West China Hospital, West China Medical School, Sichuan University, Chengdu 610041, People's Republic of China ; _publ_contact_author_email yuluot@scu.edu.cn _publ_contact_author_fax '86-28-85503301' _publ_contact_author_phone '86-28-85503817' _publ_section_title ; (2-Chloro-3,5-dinitrophenyl)(piperidin-1-yl)methanone ; _publ_section_title_footnote . loop_ _publ_author_name _publ_author_footnote _publ_author_address 'Xun Luo' . ; State Key Laboratory of Biotherapy and Cancer Center West China Hospital West China Medical School Sichuan University Chengdu 610041 People's Republic of China ; 'Yun-Chuang Huang' . ; State Key Laboratory of Biotherapy and Cancer Center West China Hospital West China Medical School Sichuan University Chengdu 610041 People's Republic of China ; 'Chao Gao' . ; State Key Laboratory of Biotherapy and Cancer Center West China Hospital West China Medical School Sichuan University Chengdu 610041 People's Republic of China ; 'Luo-Ting Yu' . ; State Key Laboratory of Biotherapy and Cancer Center West China Hospital West China Medical School Sichuan University Chengdu 610041 People's Republic of China ; _publ_section_synopsis .