data_N-methyldichloroacetamide _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C3 H5 Cl2 N O' _chemical_formula_weight 141.98 _chemical_melting_point ? _chemical_compound_source ? 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 Orthorhombic _symmetry_space_group_name_H-M Pnma loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z' '-x-1/2, y-1/2, z-1/2' _cell_length_a 9.4889(9) _cell_length_b 8.3221(6) _cell_length_c 7.7180(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 609.47(8) _cell_formula_units_Z 4 _cell_measurement_temperature 233(2) _cell_measurement_reflns_used 29 _cell_measurement_theta_min 5.71 _cell_measurement_theta_max 12.30 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.547 _exptl_crystal_density_method ? _exptl_crystal_F_000 288 _exptl_absorpt_coefficient_mu 0.949 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8279 _exptl_absorpt_correction_T_max 0.8877 _exptl_special_details ; ? ; _diffrn_ambient_temperature 233(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 'Siemens P4' _diffrn_measurement_method '2\q/\w scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1067 _diffrn_reflns_av_R_equivalents 0.0160 _diffrn_reflns_av_sigmaI/netI 0.0292 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 1 _diffrn_reflns_limit_l_min -1 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.40 _diffrn_reflns_theta_max 27.49 _reflns_number_total 745 _reflns_number_observed 611 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens SHELXTL' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0421P)^2^+0.1331P] 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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 745 _refine_ls_number_parameters 40 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0437 _refine_ls_R_factor_obs 0.0328 _refine_ls_wR_factor_all 0.0881 _refine_ls_wR_factor_obs 0.0820 _refine_ls_goodness_of_fit_all 1.070 _refine_ls_goodness_of_fit_obs 1.106 _refine_ls_restrained_S_all 1.070 _refine_ls_restrained_S_obs 1.106 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Cl1 Cl 0.32592(5) 0.42479(7) 0.02233(7) 0.0474(2) Uani 1 d . . O1 O 0.2386(2) 0.2500 -0.3151(2) 0.0397(5) Uani 1 d S . N1 N 0.4723(2) 0.2500 -0.3703(3) 0.0401(5) Uani 1 d S . H1B H 0.5564(2) 0.2500 -0.3254(3) 0.048 Uiso 1 calc SR . C2 C 0.3622(2) 0.2500 -0.2669(3) 0.0313(5) Uani 1 d S . C1 C 0.3983(2) 0.2500 -0.0735(3) 0.0337(5) Uani 1 d S . H1A H 0.5019(2) 0.2500 -0.0585(3) 0.040 Uiso 1 calc SR . C3 C 0.4572(3) 0.2500 -0.5584(4) 0.0591(10) Uani 1 d S . H3A H 0.5497(3) 0.2500 -0.6117(4) 0.089 Uiso 0.50 calc SPR . H3B H 0.4058(3) 0.3452 -0.5942(4) 0.089 Uiso 0.50 calc PR . H3C H 0.4058(3) 0.1548 -0.5942(4) 0.089 Uiso 0.00 calc PR . H4A H 0.3579(3) 0.2500 -0.5884(4) 0.089 Uiso 0.50 calc SPR . H4B H 0.5018(3) 0.1548 -0.6059(4) 0.089 Uiso 0.50 calc PR . H4C H 0.5018(3) 0.3452 -0.6059(4) 0.089 Uiso 0.00 calc PR . 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 0.0424(3) 0.0468(3) 0.0532(3) -0.0146(2) 0.0012(2) 0.0011(2) O1 0.0234(7) 0.0553(12) 0.0404(10) 0.000 -0.0041(7) 0.000 N1 0.0234(9) 0.0607(15) 0.0363(12) 0.000 -0.0035(8) 0.000 C2 0.0249(10) 0.0323(11) 0.0367(13) 0.000 -0.0020(10) 0.000 C1 0.0251(10) 0.0374(13) 0.0386(13) 0.000 -0.0031(10) 0.000 C3 0.0373(14) 0.103(3) 0.037(2) 0.000 0.0007(13) 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 C1 1.770(2) . ? O1 C2 1.230(3) . ? N1 C2 1.315(3) . ? N1 C3 1.458(4) . ? C2 C1 1.531(4) . ? C1 Cl1 1.770(2) 7_565 ? 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 N1 C3 121.7(2) . . ? O1 C2 N1 125.0(2) . . ? O1 C2 C1 120.5(2) . . ? N1 C2 C1 114.5(2) . . ? C2 C1 Cl1 108.70(10) . . ? C2 C1 Cl1 108.70(10) . 7_565 ? Cl1 C1 Cl1 110.49(14) . 7_565 ? 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C3 N1 C2 O1 0.0 . . . . ? C3 N1 C2 C1 180.0 . . . . ? O1 C2 C1 Cl1 -60.15(10) . . . . ? N1 C2 C1 Cl1 119.85(10) . . . . ? O1 C2 C1 Cl1 60.15(10) . . . 7_565 ? N1 C2 C1 Cl1 -119.85(10) . . . 7_565 ? _refine_diff_density_max 0.215 _refine_diff_density_min -0.334 _refine_diff_density_rms 0.076