# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # 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_mjh4_1d _database_code_depnum_ccdc_archive 'CCDC 916095' #TrackingRef '16272_web_deposit_cif_file_0_BillClegg_1355797042.mjh.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H2 Br2 Cl3 N O' _chemical_formula_sum 'C6 H2 Br2 Cl3 N O' _chemical_formula_weight 370.26 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' Br Br -0.2901 2.4595 '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' 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 9.971(3) _cell_length_b 16.520(4) _cell_length_c 6.6012(16) _cell_angle_alpha 90.00 _cell_angle_beta 102.18(2) _cell_angle_gamma 90.00 _cell_volume 1062.9(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 75 _cell_measurement_theta_min 2.50 _cell_measurement_theta_max 27.50 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.54 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.314 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696 _exptl_absorpt_coefficient_mu 8.338 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.094 _exptl_absorpt_correction_T_max 0.135 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD diffractometer' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21651 _diffrn_reflns_av_R_equivalents 0.0536 _diffrn_reflns_av_sigmaI/netI 0.0271 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 4.01 _diffrn_reflns_theta_max 27.57 _reflns_number_total 2433 _reflns_number_gt 1990 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Nonius COLLECT' _computing_cell_refinement 'HKL DENZO' _computing_data_reduction 'HKL DENZO' _computing_structure_solution SIR97 _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL and local programs' _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^)+(0.0038P)^2^+1.7240P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0022(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2433 _refine_ls_number_parameters 123 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0406 _refine_ls_R_factor_gt 0.0249 _refine_ls_wR_factor_ref 0.0502 _refine_ls_wR_factor_gt 0.0446 _refine_ls_goodness_of_fit_ref 1.138 _refine_ls_restrained_S_all 1.138 _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 Br1 Br 0.64716(3) 0.32144(2) -0.14075(6) 0.03433(11) Uani 1 1 d . . . Br2 Br 0.44528(3) 0.385688(19) 0.23119(5) 0.02711(9) Uani 1 1 d . . . Cl1 Cl 1.04425(9) 0.70121(5) 0.44769(13) 0.0371(2) Uani 1 1 d . . . Cl2 Cl 0.74819(8) 0.70224(4) 0.33381(11) 0.03015(18) Uani 1 1 d . . . Cl3 Cl 0.89093(7) 0.59499(4) 0.65733(10) 0.02130(15) Uani 1 1 d . . . O1 O 0.9867(2) 0.57714(12) 0.1472(3) 0.0232(4) Uani 1 1 d . . . N1 N 0.7910(2) 0.45663(14) 0.0594(4) 0.0179(5) Uani 1 1 d . . . H1 H 0.850(3) 0.4507(18) -0.004(5) 0.020(8) Uiso 1 1 d . . . C1 C 0.6820(3) 0.40742(17) 0.0461(4) 0.0196(6) Uani 1 1 d . . . C2 C 0.6073(3) 0.43312(17) 0.1882(4) 0.0200(6) Uani 1 1 d . . . C3 C 0.6739(3) 0.50035(17) 0.2917(4) 0.0195(6) Uani 1 1 d . . . H3A H 0.6456 0.5307 0.3976 0.023 Uiso 1 1 calc R . . C4 C 0.7898(3) 0.51446(16) 0.2104(4) 0.0168(5) Uani 1 1 d . . . C5 C 0.8968(3) 0.57472(16) 0.2467(4) 0.0161(5) Uani 1 1 d . . . C6 C 0.8963(3) 0.64093(16) 0.4155(4) 0.0181(6) Uani 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 Br1 0.02473(17) 0.03287(18) 0.0449(2) -0.02196(15) 0.00635(14) -0.00270(13) Br2 0.01790(15) 0.03020(17) 0.03518(18) -0.00326(13) 0.01002(12) -0.00740(12) Cl1 0.0435(5) 0.0392(5) 0.0335(4) -0.0129(3) 0.0190(4) -0.0261(4) Cl2 0.0435(4) 0.0217(4) 0.0244(4) 0.0012(3) 0.0051(3) 0.0151(3) Cl3 0.0221(3) 0.0267(4) 0.0155(3) 0.0045(3) 0.0046(3) 0.0013(3) O1 0.0251(11) 0.0222(10) 0.0269(11) -0.0025(8) 0.0155(9) -0.0022(8) N1 0.0133(11) 0.0208(12) 0.0215(12) -0.0050(10) 0.0081(10) 0.0006(9) C1 0.0170(13) 0.0195(14) 0.0218(14) -0.0054(11) 0.0027(11) -0.0001(11) C2 0.0148(13) 0.0220(14) 0.0238(15) -0.0011(11) 0.0057(11) -0.0020(11) C3 0.0185(13) 0.0204(14) 0.0212(14) -0.0035(11) 0.0081(11) 0.0001(11) C4 0.0168(13) 0.0170(13) 0.0181(13) -0.0011(10) 0.0068(11) 0.0004(10) C5 0.0172(13) 0.0157(13) 0.0161(13) 0.0034(10) 0.0050(11) 0.0045(10) C6 0.0220(14) 0.0160(13) 0.0174(14) 0.0001(10) 0.0073(11) -0.0021(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 Br1 C1 1.865(3) . ? Br2 C2 1.870(3) . ? Cl1 C6 1.755(3) . ? Cl2 C6 1.778(3) . ? Cl3 C6 1.778(3) . ? O1 C5 1.218(3) . ? N1 H1 0.80(3) . ? N1 C1 1.344(3) . ? N1 C4 1.382(3) . ? C1 C2 1.382(4) . ? C2 C3 1.397(4) . ? C3 H3A 0.950 . ? C3 C4 1.393(4) . ? C4 C5 1.442(4) . ? C5 C6 1.563(4) . ? 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 H1 N1 C1 125(2) . . ? H1 N1 C4 126(2) . . ? C1 N1 C4 109.6(2) . . ? Br1 C1 N1 122.6(2) . . ? Br1 C1 C2 129.1(2) . . ? N1 C1 C2 108.3(2) . . ? Br2 C2 C1 125.5(2) . . ? Br2 C2 C3 126.6(2) . . ? C1 C2 C3 107.9(2) . . ? C2 C3 H3A 126.5 . . ? C2 C3 C4 107.0(2) . . ? H3A C3 C4 126.5 . . ? N1 C4 C3 107.2(2) . . ? N1 C4 C5 118.6(2) . . ? C3 C4 C5 134.2(2) . . ? O1 C5 C4 122.4(2) . . ? O1 C5 C6 118.4(2) . . ? C4 C5 C6 119.2(2) . . ? Cl1 C6 Cl2 109.66(15) . . ? Cl1 C6 Cl3 108.51(15) . . ? Cl1 C6 C5 110.74(18) . . ? Cl2 C6 Cl3 109.57(14) . . ? Cl2 C6 C5 108.05(18) . . ? Cl3 C6 C5 110.30(18) . . ? 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 C4 N1 C1 Br1 179.90(19) . . . . ? C4 N1 C1 C2 0.5(3) . . . . ? Br1 C1 C2 Br2 0.2(4) . . . . ? Br1 C1 C2 C3 -179.6(2) . . . . ? N1 C1 C2 Br2 179.6(2) . . . . ? N1 C1 C2 C3 -0.2(3) . . . . ? Br2 C2 C3 C4 -180.0(2) . . . . ? C1 C2 C3 C4 -0.2(3) . . . . ? C1 N1 C4 C3 -0.6(3) . . . . ? C1 N1 C4 C5 -178.7(2) . . . . ? C2 C3 C4 N1 0.5(3) . . . . ? C2 C3 C4 C5 178.1(3) . . . . ? N1 C4 C5 O1 1.1(4) . . . . ? N1 C4 C5 C6 179.5(2) . . . . ? C3 C4 C5 O1 -176.3(3) . . . . ? C3 C4 C5 C6 2.1(5) . . . . ? O1 C5 C6 Cl1 -7.0(3) . . . . ? O1 C5 C6 Cl2 113.1(2) . . . . ? O1 C5 C6 Cl3 -127.1(2) . . . . ? C4 C5 C6 Cl1 174.6(2) . . . . ? C4 C5 C6 Cl2 -65.3(3) . . . . ? C4 C5 C6 Cl3 54.4(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O1 0.80(3) 2.10(3) 2.892(3) 173(3) 3_765 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.703 _refine_diff_density_min -0.865 _refine_diff_density_rms 0.108 data_mjh78_3a _database_code_depnum_ccdc_archive 'CCDC 916096' #TrackingRef '16272_web_deposit_cif_file_0_BillClegg_1355797042.mjh.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H13 Cl2 N O2' _chemical_formula_sum 'C14 H13 Cl2 N O2' _chemical_formula_weight 298.15 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 'P b c n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 21.1956(11) _cell_length_b 7.5271(4) _cell_length_c 17.1302(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2733.0(3) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3920 _cell_measurement_theta_min 2.87 _cell_measurement_theta_max 28.61 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.449 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1232 _exptl_absorpt_coefficient_mu 0.471 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.872 _exptl_absorpt_correction_T_max 0.912 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube with Enhance optics' _diffrn_radiation_monochromator none _diffrn_measurement_device_type 'Oxford Diffraction Gemini A Ultra diffractometer' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3968 _diffrn_reflns_number 9986 _diffrn_reflns_av_R_equivalents 0.0337 _diffrn_reflns_av_sigmaI/netI 0.0342 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.87 _diffrn_reflns_theta_max 28.64 _reflns_number_total 2977 _reflns_number_gt 2347 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL and local programs' _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^)+(0.0457P)^2^+1.9653P] 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 2977 _refine_ls_number_parameters 177 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0606 _refine_ls_R_factor_gt 0.0429 _refine_ls_wR_factor_ref 0.1091 _refine_ls_wR_factor_gt 0.0981 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _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 0.36856(3) 0.33388(7) 0.15066(3) 0.03307(17) Uani 1 1 d . . . Cl2 Cl 0.30354(2) 0.11348(8) 0.03655(3) 0.03294(16) Uani 1 1 d . . . O1 O 0.45936(9) 0.1490(3) -0.01866(11) 0.0487(5) Uani 1 1 d . . . O2 O 0.47200(8) 0.0518(3) 0.13511(10) 0.0372(4) Uani 1 1 d . . . H2 H 0.4960(16) 0.038(4) 0.098(2) 0.072(11) Uiso 1 1 d . . . N N 0.43398(10) 0.4797(3) -0.09231(12) 0.0378(5) Uani 1 1 d . . . C1 C 0.48997(13) 0.4064(4) -0.12988(16) 0.0473(7) Uani 1 1 d . . . H1A H 0.5054 0.4901 -0.1693 0.071 Uiso 1 1 calc R . . H1B H 0.4793 0.2934 -0.1550 0.071 Uiso 1 1 calc R . . H1C H 0.5229 0.3866 -0.0906 0.071 Uiso 1 1 calc R . . C2 C 0.40511(15) 0.6303(4) -0.11512(18) 0.0509(7) Uani 1 1 d . . . H2A H 0.4185 0.7033 -0.1572 0.061 Uiso 1 1 calc R . . C3 C 0.35388(14) 0.6628(4) -0.06903(17) 0.0503(7) Uani 1 1 d . . . H3 H 0.3256 0.7604 -0.0733 0.060 Uiso 1 1 calc R . . C4 C 0.35088(12) 0.5266(3) -0.01479(15) 0.0387(6) Uani 1 1 d . . . H4 H 0.3200 0.5139 0.0251 0.046 Uiso 1 1 calc R . . C5 C 0.40089(11) 0.4117(3) -0.02887(13) 0.0324(5) Uani 1 1 d . . . C6 C 0.41768(10) 0.2452(3) 0.00608(13) 0.0308(5) Uani 1 1 d . . . C7 C 0.37911(10) 0.1717(3) 0.07638(12) 0.0266(5) Uani 1 1 d . . . C8 C 0.41036(10) 0.0035(3) 0.11089(13) 0.0283(5) Uani 1 1 d . . . H8 H 0.4139 -0.0877 0.0687 0.034 Uiso 1 1 calc R . . C9 C 0.37512(10) -0.0771(3) 0.17880(13) 0.0276(5) Uani 1 1 d . . . C10 C 0.39203(11) -0.0343(3) 0.25466(14) 0.0327(5) Uani 1 1 d . . . H10 H 0.4258 0.0459 0.2640 0.039 Uiso 1 1 calc R . . C11 C 0.35973(12) -0.1084(3) 0.31687(15) 0.0398(6) Uani 1 1 d . . . H11 H 0.3713 -0.0778 0.3687 0.048 Uiso 1 1 calc R . . C12 C 0.31104(12) -0.2261(4) 0.30432(15) 0.0414(6) Uani 1 1 d . . . H12 H 0.2890 -0.2758 0.3474 0.050 Uiso 1 1 calc R . . C13 C 0.29436(12) -0.2718(3) 0.22899(16) 0.0410(6) Uani 1 1 d . . . H13 H 0.2612 -0.3541 0.2199 0.049 Uiso 1 1 calc R . . C14 C 0.32644(12) -0.1966(3) 0.16699(14) 0.0337(5) Uani 1 1 d . . . H14 H 0.3148 -0.2276 0.1152 0.040 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0394(3) 0.0304(3) 0.0294(3) -0.0066(2) 0.0073(2) 0.0006(2) Cl2 0.0271(3) 0.0385(3) 0.0332(3) -0.0005(2) -0.0036(2) 0.0012(2) O1 0.0467(10) 0.0614(12) 0.0380(10) 0.0139(9) 0.0190(8) 0.0270(10) O2 0.0278(8) 0.0564(11) 0.0273(9) -0.0015(8) 0.0012(7) 0.0052(8) N 0.0433(11) 0.0370(11) 0.0331(12) -0.0001(9) 0.0051(9) -0.0074(10) C1 0.0472(15) 0.0536(16) 0.0410(16) 0.0030(13) 0.0136(12) -0.0138(13) C2 0.071(2) 0.0363(14) 0.0453(17) 0.0085(12) 0.0005(14) -0.0091(14) C3 0.0643(18) 0.0344(14) 0.0524(18) 0.0055(12) -0.0016(14) 0.0099(13) C4 0.0434(14) 0.0372(13) 0.0356(14) -0.0019(11) 0.0000(11) 0.0050(12) C5 0.0344(12) 0.0343(13) 0.0284(12) -0.0006(10) 0.0018(9) -0.0033(10) C6 0.0289(11) 0.0383(13) 0.0252(12) -0.0001(9) 0.0025(9) 0.0025(10) C7 0.0242(10) 0.0328(12) 0.0228(11) -0.0052(9) 0.0029(8) 0.0016(9) C8 0.0281(11) 0.0338(12) 0.0230(12) -0.0041(9) -0.0009(9) 0.0059(10) C9 0.0315(11) 0.0292(11) 0.0221(11) -0.0030(9) -0.0003(9) 0.0079(10) C10 0.0385(12) 0.0323(12) 0.0274(12) -0.0047(10) -0.0027(10) 0.0019(11) C11 0.0531(15) 0.0429(14) 0.0233(12) 0.0020(10) 0.0000(11) 0.0044(13) C12 0.0496(15) 0.0410(14) 0.0337(14) 0.0115(11) 0.0072(11) 0.0031(13) C13 0.0432(14) 0.0330(13) 0.0469(16) 0.0067(11) -0.0031(12) -0.0051(11) C14 0.0427(13) 0.0285(12) 0.0298(13) -0.0037(9) -0.0047(10) 0.0001(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 C7 1.777(2) . ? Cl2 C7 1.795(2) . ? O1 C6 1.218(3) . ? O2 H2 0.82(4) . ? O2 C8 1.418(3) . ? N C1 1.458(3) . ? N C2 1.346(3) . ? N C5 1.391(3) . ? C1 H1A 0.980 . ? C1 H1B 0.980 . ? C1 H1C 0.980 . ? C2 H2A 0.950 . ? C2 C3 1.365(4) . ? C3 H3 0.950 . ? C3 C4 1.385(4) . ? C4 H4 0.950 . ? C4 C5 1.389(3) . ? C5 C6 1.434(3) . ? C6 C7 1.557(3) . ? C7 C8 1.546(3) . ? C8 H8 1.000 . ? C8 C9 1.510(3) . ? C9 C10 1.386(3) . ? C9 C14 1.384(3) . ? C10 H10 0.950 . ? C10 C11 1.384(3) . ? C11 H11 0.950 . ? C11 C12 1.377(4) . ? C12 H12 0.950 . ? C12 C13 1.382(4) . ? C13 H13 0.950 . ? C13 C14 1.382(3) . ? C14 H14 0.950 . ? 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 H2 O2 C8 108(2) . . ? C1 N C2 124.1(2) . . ? C1 N C5 128.0(2) . . ? C2 N C5 107.9(2) . . ? N C1 H1A 109.5 . . ? N C1 H1B 109.5 . . ? N C1 H1C 109.5 . . ? H1A C1 H1B 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N C2 H2A 124.9 . . ? N C2 C3 110.2(2) . . ? H2A C2 C3 124.9 . . ? C2 C3 H3 126.5 . . ? C2 C3 C4 106.9(2) . . ? H3 C3 C4 126.5 . . ? C3 C4 H4 126.0 . . ? C3 C4 C5 108.0(2) . . ? H4 C4 C5 126.0 . . ? N C5 C4 107.0(2) . . ? N C5 C6 121.5(2) . . ? C4 C5 C6 131.4(2) . . ? O1 C6 C5 123.6(2) . . ? O1 C6 C7 116.0(2) . . ? C5 C6 C7 120.21(19) . . ? Cl1 C7 Cl2 109.11(11) . . ? Cl1 C7 C6 112.08(15) . . ? Cl1 C7 C8 110.03(15) . . ? Cl2 C7 C6 105.14(14) . . ? Cl2 C7 C8 109.12(15) . . ? C6 C7 C8 111.20(17) . . ? O2 C8 C7 107.25(18) . . ? O2 C8 H8 108.5 . . ? O2 C8 C9 109.48(18) . . ? C7 C8 H8 108.5 . . ? C7 C8 C9 114.33(17) . . ? H8 C8 C9 108.5 . . ? C8 C9 C10 120.1(2) . . ? C8 C9 C14 121.2(2) . . ? C10 C9 C14 118.7(2) . . ? C9 C10 H10 120.0 . . ? C9 C10 C11 120.0(2) . . ? H10 C10 C11 120.0 . . ? C10 C11 H11 119.7 . . ? C10 C11 C12 120.6(2) . . ? H11 C11 C12 119.7 . . ? C11 C12 H12 120.1 . . ? C11 C12 C13 119.9(2) . . ? H12 C12 C13 120.1 . . ? C12 C13 H13 120.3 . . ? C12 C13 C14 119.3(2) . . ? H13 C13 C14 120.3 . . ? C9 C14 C13 121.4(2) . . ? C9 C14 H14 119.3 . . ? C13 C14 H14 119.3 . . ? 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 C1 N C2 C3 179.4(2) . . . . ? C5 N C2 C3 -0.4(3) . . . . ? N C2 C3 C4 0.3(3) . . . . ? C2 C3 C4 C5 0.0(3) . . . . ? C3 C4 C5 N -0.2(3) . . . . ? C3 C4 C5 C6 -175.4(3) . . . . ? C1 N C5 C4 -179.5(2) . . . . ? C1 N C5 C6 -3.7(4) . . . . ? C2 N C5 C4 0.4(3) . . . . ? C2 N C5 C6 176.1(2) . . . . ? N C5 C6 O1 -3.3(4) . . . . ? N C5 C6 C7 -179.2(2) . . . . ? C4 C5 C6 O1 171.3(3) . . . . ? C4 C5 C6 C7 -4.6(4) . . . . ? O1 C6 C7 Cl1 134.5(2) . . . . ? O1 C6 C7 Cl2 -107.1(2) . . . . ? O1 C6 C7 C8 10.9(3) . . . . ? C5 C6 C7 Cl1 -49.3(3) . . . . ? C5 C6 C7 Cl2 69.1(2) . . . . ? C5 C6 C7 C8 -173.0(2) . . . . ? Cl1 C7 C8 O2 -65.58(19) . . . . ? Cl1 C7 C8 C9 56.0(2) . . . . ? Cl2 C7 C8 O2 174.74(14) . . . . ? Cl2 C7 C8 C9 -63.7(2) . . . . ? C6 C7 C8 O2 59.2(2) . . . . ? C6 C7 C8 C9 -179.21(18) . . . . ? O2 C8 C9 C10 25.1(3) . . . . ? O2 C8 C9 C14 -153.8(2) . . . . ? C7 C8 C9 C10 -95.3(2) . . . . ? C7 C8 C9 C14 85.9(3) . . . . ? C8 C9 C10 C11 -180.0(2) . . . . ? C14 C9 C10 C11 -1.1(3) . . . . ? C9 C10 C11 C12 0.6(4) . . . . ? C10 C11 C12 C13 0.4(4) . . . . ? C11 C12 C13 C14 -0.8(4) . . . . ? C12 C13 C14 C9 0.3(4) . . . . ? C8 C9 C14 C13 179.5(2) . . . . ? C10 C9 C14 C13 0.6(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H2 O1 0.82(4) 2.17(3) 2.895(2) 147(3) 5_655 O2 H2 O1 0.82(4) 2.30(4) 2.747(3) 115(3) . _diffrn_measured_fraction_theta_max 0.847 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.489 _refine_diff_density_min -0.239 _refine_diff_density_rms 0.058 # Contents of RES file _computing_special_details ; TITL mjh78 in Pbcn CELL 0.71073 21.1956 7.5271 17.1302 90.000 90.000 90.000 ZERR 8.00 0.0011 0.0004 0.0014 0.000 0.000 0.000 LATT 1 SYMM 0.5-X, 0.5-Y, 0.5+Z SYMM -X, Y, 0.5-Z SYMM 0.5+X, 0.5-Y, -Z SFAC C H N O CL UNIT 112 104 8 16 16 TEMP -123 L.S. 8 BOND $H CONF REM colourless block SIZE 0.30 0.20 0.20 ACTA 50 FMAP 2 PLAN 5 HTAB O2 O1_$1 EQIV $1 -x+1, -y, -z HTAB O2 O1 REM EXTI 0.000088 WGHT 0.045700 1.965300 FVAR 0.24719 CL1 5 0.368559 0.333884 0.150662 11.00000 0.03940 0.03042 = 0.02939 -0.00664 0.00728 0.00059 CL2 5 0.303536 0.113477 0.036550 11.00000 0.02713 0.03845 = 0.03323 -0.00048 -0.00362 0.00116 O1 4 0.459362 0.149001 -0.018661 11.00000 0.04668 0.06142 = 0.03804 0.01387 0.01900 0.02701 O2 4 0.472002 0.051825 0.135106 11.00000 0.02784 0.05638 = 0.02728 -0.00148 0.00118 0.00516 H2 2 0.495975 0.037739 0.097691 11.00000 0.07242 N 3 0.433981 0.479666 -0.092307 11.00000 0.04334 0.03701 = 0.03308 -0.00014 0.00513 -0.00738 C1 1 0.489974 0.406440 -0.129879 11.00000 0.04717 0.05363 = 0.04096 0.00300 0.01364 -0.01377 AFIX 137 H1A 2 0.505427 0.490119 -0.169317 11.00000 -1.50000 H1B 2 0.479270 0.293370 -0.154959 11.00000 -1.50000 H1C 2 0.522854 0.386622 -0.090612 11.00000 -1.50000 AFIX 0 C2 1 0.405114 0.630276 -0.115120 11.00000 0.07101 0.03632 = 0.04532 0.00851 0.00054 -0.00913 AFIX 43 H2A 2 0.418473 0.703330 -0.157214 11.00000 -1.20000 AFIX 0 C3 1 0.353878 0.662839 -0.069028 11.00000 0.06425 0.03437 = 0.05240 0.00548 -0.00163 0.00990 AFIX 43 H3 2 0.325645 0.760373 -0.073323 11.00000 -1.20000 AFIX 0 C4 1 0.350883 0.526582 -0.014790 11.00000 0.04341 0.03718 = 0.03564 -0.00190 -0.00002 0.00498 AFIX 43 H4 2 0.320031 0.513922 0.025052 11.00000 -1.20000 AFIX 0 C5 1 0.400891 0.411727 -0.028869 11.00000 0.03438 0.03433 = 0.02844 -0.00059 0.00185 -0.00328 C6 1 0.417676 0.245169 0.006082 11.00000 0.02894 0.03828 = 0.02518 -0.00006 0.00252 0.00249 C7 1 0.379114 0.171711 0.076380 11.00000 0.02421 0.03278 = 0.02276 -0.00519 0.00290 0.00158 C8 1 0.410355 0.003534 0.110893 11.00000 0.02813 0.03383 = 0.02297 -0.00408 -0.00088 0.00590 AFIX 13 H8 2 0.413907 -0.087706 0.068689 11.00000 -1.20000 AFIX 0 C9 1 0.375117 -0.077119 0.178795 11.00000 0.03146 0.02916 = 0.02209 -0.00297 -0.00029 0.00786 C10 1 0.392027 -0.034343 0.254656 11.00000 0.03845 0.03233 = 0.02739 -0.00466 -0.00267 0.00188 AFIX 43 H10 2 0.425807 0.045868 0.263951 11.00000 -1.20000 AFIX 0 C11 1 0.359735 -0.108404 0.316871 11.00000 0.05309 0.04293 = 0.02334 0.00195 -0.00001 0.00436 AFIX 43 H11 2 0.371271 -0.077755 0.368740 11.00000 -1.20000 AFIX 0 C12 1 0.311041 -0.226098 0.304320 11.00000 0.04962 0.04103 = 0.03369 0.01150 0.00720 0.00314 AFIX 43 H12 2 0.288966 -0.275761 0.347369 11.00000 -1.20000 AFIX 0 C13 1 0.294360 -0.271796 0.228986 11.00000 0.04324 0.03298 = 0.04687 0.00673 -0.00309 -0.00515 AFIX 43 H13 2 0.261176 -0.354067 0.219888 11.00000 -1.20000 AFIX 0 C14 1 0.326436 -0.196620 0.166989 11.00000 0.04274 0.02855 = 0.02977 -0.00366 -0.00466 0.00010 AFIX 43 H14 2 0.314818 -0.227640 0.115190 11.00000 -1.20000 HKLF 4 REM mjh78 in Pbcn REM R1 = 0.0429 for 2347 Fo > 4sig(Fo) and 0.0606 for all 2977 data REM 177 parameters refined using 0 restraints END ; data_mjh76_3b _database_code_depnum_ccdc_archive 'CCDC 916097' #TrackingRef '16272_web_deposit_cif_file_0_BillClegg_1355797042.mjh.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H15 Cl2 N O3' _chemical_formula_sum 'C15 H15 Cl2 N O3' _chemical_formula_weight 328.18 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/n' 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 8.9648(6) _cell_length_b 12.0920(7) _cell_length_c 14.0270(11) _cell_angle_alpha 90.00 _cell_angle_beta 106.344(8) _cell_angle_gamma 90.00 _cell_volume 1459.11(17) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3062 _cell_measurement_theta_min 2.90 _cell_measurement_theta_max 28.37 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.494 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 0.454 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.839 _exptl_absorpt_correction_T_max 0.876 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube with Enhance optics' _diffrn_radiation_monochromator none _diffrn_measurement_device_type 'Oxford Diffraction Gemini A Ultra diffractometer' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3968 _diffrn_reflns_number 9278 _diffrn_reflns_av_R_equivalents 0.0284 _diffrn_reflns_av_sigmaI/netI 0.0348 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.91 _diffrn_reflns_theta_max 28.43 _reflns_number_total 3145 _reflns_number_gt 2539 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL and local programs' _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^)+(0.0342P)^2^+0.6168P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3145 _refine_ls_number_parameters 196 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0509 _refine_ls_R_factor_gt 0.0369 _refine_ls_wR_factor_ref 0.0868 _refine_ls_wR_factor_gt 0.0784 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _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 Cl2 Cl 0.04358(5) 0.17039(4) 0.09179(3) 0.02894(13) Uani 1 1 d . . . O4 O 0.68450(14) 0.04804(10) 0.40294(10) 0.0291(3) Uani 1 1 d . . . Cl1 Cl -0.05052(6) -0.04115(4) 0.15533(4) 0.03477(15) Uani 1 1 d . . . C7 C -0.0514(2) 0.10504(14) 0.17291(14) 0.0240(4) Uani 1 1 d . . . O1 O -0.26157(15) 0.19557(12) 0.21180(10) 0.0338(3) Uani 1 1 d . . . O2 O -0.02943(17) 0.08008(13) 0.34767(11) 0.0364(4) Uani 1 1 d . . . C11 C 0.4199(2) -0.02164(15) 0.36889(14) 0.0260(4) Uani 1 1 d . . . H11A H 0.4544 -0.0949 0.3875 0.031 Uiso 1 1 calc R . . N N -0.47373(18) 0.17147(13) 0.01733(12) 0.0309(4) Uani 1 1 d . . . C14 C 0.3175(2) 0.19123(15) 0.31509(14) 0.0254(4) Uani 1 1 d . . . H14A H 0.2832 0.2647 0.2972 0.030 Uiso 1 1 calc R . . C12 C 0.5268(2) 0.06214(15) 0.37217(13) 0.0230(4) Uani 1 1 d . . . C6 C -0.2227(2) 0.14796(15) 0.14549(14) 0.0254(4) Uani 1 1 d . . . C9 C 0.2086(2) 0.10787(15) 0.31024(13) 0.0235(4) Uani 1 1 d . . . C10 C 0.2625(2) 0.00213(16) 0.33824(14) 0.0277(4) Uani 1 1 d . . . H10A H 0.1897 -0.0555 0.3364 0.033 Uiso 1 1 calc R . . C15 C 0.7405(2) -0.06237(16) 0.42445(16) 0.0336(5) Uani 1 1 d . . . H15A H 0.8541 -0.0614 0.4499 0.050 Uiso 1 1 calc R . . H15B H 0.7097 -0.1069 0.3637 0.050 Uiso 1 1 calc R . . H15C H 0.6961 -0.0946 0.4745 0.050 Uiso 1 1 calc R . . C8 C 0.0376(2) 0.13513(16) 0.28105(14) 0.0253(4) Uani 1 1 d . . . H8A H 0.0266 0.2165 0.2897 0.030 Uiso 1 1 calc R . . C13 C 0.4749(2) 0.16867(15) 0.34557(14) 0.0267(4) Uani 1 1 d . . . H13A H 0.5478 0.2264 0.3483 0.032 Uiso 1 1 calc R . . C4 C -0.2981(2) 0.07495(16) -0.03360(15) 0.0325(5) Uani 1 1 d . . . H4A H -0.2047 0.0391 -0.0356 0.039 Uiso 1 1 calc R . . C3 C -0.4345(3) 0.07963(18) -0.11077(16) 0.0391(5) Uani 1 1 d . . . H3A H -0.4522 0.0474 -0.1748 0.047 Uiso 1 1 calc R . . C5 C -0.3217(2) 0.13179(15) 0.04724(14) 0.0267(4) Uani 1 1 d . . . C1 C -0.5563(2) 0.23437(19) 0.07529(17) 0.0400(5) Uani 1 1 d . . . H1A H -0.6562 0.2596 0.0318 0.060 Uiso 1 1 calc R . . H1B H -0.4938 0.2985 0.1053 0.060 Uiso 1 1 calc R . . H1C H -0.5745 0.1872 0.1278 0.060 Uiso 1 1 calc R . . C2 C -0.5389(2) 0.13963(18) -0.07703(16) 0.0384(5) Uani 1 1 d . . . H2A H -0.6422 0.1563 -0.1148 0.046 Uiso 1 1 calc R . . H2 H -0.122(3) 0.103(2) 0.3381(19) 0.056(8) 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 Cl2 0.0271(2) 0.0297(3) 0.0338(3) -0.0009(2) 0.0146(2) -0.00252(19) O4 0.0194(6) 0.0265(7) 0.0413(8) 0.0020(6) 0.0081(6) 0.0023(5) Cl1 0.0291(3) 0.0181(2) 0.0528(3) -0.0019(2) 0.0045(2) 0.00063(18) C7 0.0232(9) 0.0165(8) 0.0354(10) 0.0019(8) 0.0131(8) -0.0008(7) O1 0.0278(7) 0.0401(8) 0.0355(7) -0.0001(6) 0.0122(6) 0.0090(6) O2 0.0231(7) 0.0507(9) 0.0387(8) 0.0132(7) 0.0139(6) 0.0052(7) C11 0.0253(9) 0.0206(9) 0.0327(10) 0.0048(8) 0.0091(8) 0.0026(7) N 0.0208(8) 0.0349(9) 0.0373(9) 0.0109(8) 0.0084(7) -0.0020(7) C14 0.0261(9) 0.0192(9) 0.0321(10) -0.0003(8) 0.0100(8) 0.0020(7) C12 0.0200(9) 0.0259(9) 0.0242(9) -0.0009(8) 0.0080(7) 0.0008(7) C6 0.0227(9) 0.0221(9) 0.0332(10) 0.0048(8) 0.0107(8) -0.0003(7) C9 0.0210(9) 0.0261(9) 0.0252(9) -0.0003(8) 0.0094(8) 0.0013(7) C10 0.0240(9) 0.0244(9) 0.0358(10) 0.0043(8) 0.0103(8) -0.0021(8) C15 0.0264(10) 0.0306(10) 0.0428(11) 0.0035(9) 0.0080(9) 0.0084(8) C8 0.0217(9) 0.0254(9) 0.0310(10) 0.0022(8) 0.0108(8) 0.0016(7) C13 0.0238(9) 0.0219(9) 0.0353(10) -0.0012(8) 0.0096(8) -0.0038(7) C4 0.0334(11) 0.0273(10) 0.0376(11) 0.0016(9) 0.0111(9) -0.0042(8) C3 0.0440(13) 0.0375(12) 0.0333(11) 0.0029(9) 0.0070(10) -0.0124(10) C5 0.0221(9) 0.0231(9) 0.0360(10) 0.0053(8) 0.0100(8) -0.0021(7) C1 0.0205(10) 0.0520(13) 0.0492(13) 0.0104(11) 0.0124(9) 0.0068(9) C2 0.0272(11) 0.0447(12) 0.0387(12) 0.0137(10) 0.0020(9) -0.0095(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 Cl2 C7 1.7856(18) . ? O4 C12 1.368(2) . ? O4 C15 1.428(2) . ? Cl1 C7 1.7852(18) . ? C7 C6 1.564(2) . ? C7 C8 1.545(3) . ? O1 C6 1.225(2) . ? O2 C8 1.412(2) . ? O2 H2 0.85(3) . ? C11 H11A 0.950 . ? C11 C12 1.387(2) . ? C11 C10 1.385(3) . ? N C5 1.393(2) . ? N C1 1.458(3) . ? N C2 1.344(3) . ? C14 H14A 0.950 . ? C14 C9 1.392(3) . ? C14 C13 1.381(3) . ? C12 C13 1.385(2) . ? C6 C5 1.427(3) . ? C9 C10 1.384(3) . ? C9 C8 1.508(2) . ? C10 H10A 0.950 . ? C15 H15A 0.980 . ? C15 H15B 0.980 . ? C15 H15C 0.980 . ? C8 H8A 1.000 . ? C13 H13A 0.950 . ? C4 H4A 0.950 . ? C4 C3 1.388(3) . ? C4 C5 1.392(3) . ? C3 H3A 0.950 . ? C3 C2 1.369(3) . ? C1 H1A 0.980 . ? C1 H1B 0.980 . ? C1 H1C 0.980 . ? C2 H2A 0.950 . ? 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 C12 O4 C15 117.00(14) . . ? Cl2 C7 Cl1 109.20(10) . . ? Cl2 C7 C6 107.93(12) . . ? Cl2 C7 C8 108.34(12) . . ? Cl1 C7 C6 109.68(12) . . ? Cl1 C7 C8 110.34(12) . . ? C6 C7 C8 111.29(15) . . ? C8 O2 H2 108.6(18) . . ? H11A C11 C12 120.2 . . ? H11A C11 C10 120.2 . . ? C12 C11 C10 119.56(17) . . ? C5 N C1 128.22(17) . . ? C5 N C2 108.37(17) . . ? C1 N C2 123.39(17) . . ? H14A C14 C9 119.6 . . ? H14A C14 C13 119.6 . . ? C9 C14 C13 120.89(16) . . ? O4 C12 C11 124.26(16) . . ? O4 C12 C13 116.12(16) . . ? C11 C12 C13 119.59(16) . . ? C7 C6 O1 116.03(16) . . ? C7 C6 C5 119.55(16) . . ? O1 C6 C5 124.41(17) . . ? C14 C9 C10 118.14(16) . . ? C14 C9 C8 120.05(16) . . ? C10 C9 C8 121.71(16) . . ? C11 C10 C9 121.56(17) . . ? C11 C10 H10A 119.2 . . ? C9 C10 H10A 119.2 . . ? O4 C15 H15A 109.5 . . ? O4 C15 H15B 109.5 . . ? O4 C15 H15C 109.5 . . ? H15A C15 H15B 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C7 C8 O2 109.92(15) . . ? C7 C8 C9 114.79(15) . . ? C7 C8 H8A 108.0 . . ? O2 C8 C9 107.86(15) . . ? O2 C8 H8A 108.0 . . ? C9 C8 H8A 108.0 . . ? C14 C13 C12 120.25(17) . . ? C14 C13 H13A 119.9 . . ? C12 C13 H13A 119.9 . . ? H4A C4 C3 125.9 . . ? H4A C4 C5 125.9 . . ? C3 C4 C5 108.21(19) . . ? C4 C3 H3A 126.6 . . ? C4 C3 C2 106.85(19) . . ? H3A C3 C2 126.6 . . ? N C5 C6 122.24(17) . . ? N C5 C4 106.55(17) . . ? C6 C5 C4 131.17(18) . . ? N C1 H1A 109.5 . . ? N C1 H1B 109.5 . . ? N C1 H1C 109.5 . . ? H1A C1 H1B 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N C2 C3 110.03(18) . . ? N C2 H2A 125.0 . . ? C3 C2 H2A 125.0 . . ? 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 C15 O4 C12 C11 5.7(3) . . . . ? C15 O4 C12 C13 -175.98(17) . . . . ? C10 C11 C12 O4 178.77(17) . . . . ? C10 C11 C12 C13 0.5(3) . . . . ? Cl2 C7 C6 O1 -120.13(16) . . . . ? Cl2 C7 C6 C5 58.86(19) . . . . ? Cl1 C7 C6 O1 120.99(16) . . . . ? Cl1 C7 C6 C5 -60.01(19) . . . . ? C8 C7 C6 O1 -1.4(2) . . . . ? C8 C7 C6 C5 177.61(15) . . . . ? C13 C14 C9 C10 1.0(3) . . . . ? C13 C14 C9 C8 177.34(17) . . . . ? C14 C9 C10 C11 -1.0(3) . . . . ? C8 C9 C10 C11 -177.32(17) . . . . ? C12 C11 C10 C9 0.3(3) . . . . ? C14 C9 C8 C7 102.5(2) . . . . ? C14 C9 C8 O2 -134.64(17) . . . . ? C10 C9 C8 C7 -81.3(2) . . . . ? C10 C9 C8 O2 41.6(2) . . . . ? Cl2 C7 C8 O2 -176.91(12) . . . . ? Cl2 C7 C8 C9 -55.12(18) . . . . ? Cl1 C7 C8 O2 -57.41(17) . . . . ? Cl1 C7 C8 C9 64.38(17) . . . . ? C6 C7 C8 O2 64.58(19) . . . . ? C6 C7 C8 C9 -173.63(14) . . . . ? C9 C14 C13 C12 -0.2(3) . . . . ? O4 C12 C13 C14 -178.94(16) . . . . ? C11 C12 C13 C14 -0.6(3) . . . . ? C5 C4 C3 C2 0.6(2) . . . . ? C3 C4 C5 N -0.5(2) . . . . ? C3 C4 C5 C6 176.98(19) . . . . ? C1 N C5 C6 0.9(3) . . . . ? C1 N C5 C4 178.64(18) . . . . ? C2 N C5 C6 -177.50(17) . . . . ? C2 N C5 C4 0.3(2) . . . . ? C7 C6 C5 N -177.72(16) . . . . ? C7 C6 C5 C4 5.1(3) . . . . ? O1 C6 C5 N 1.2(3) . . . . ? O1 C6 C5 C4 -175.96(19) . . . . ? C5 N C2 C3 0.1(2) . . . . ? C1 N C2 C3 -178.39(18) . . . . ? C4 C3 C2 N -0.4(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H2 O1 0.85(3) 2.17(3) 2.772(2) 128(2) . O2 H2 O4 0.85(3) 2.28(3) 2.9064(19) 131(2) 1_455 _diffrn_measured_fraction_theta_max 0.858 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.318 _refine_diff_density_min -0.208 _refine_diff_density_rms 0.053 # Contents of RES file _computing_special_details ; TITL mjh76 in P2(1)/n CELL 0.71073 8.9648 12.0920 14.0270 90.000 106.344 90.000 ZERR 4.00 0.0006 0.0007 0.0011 0.000 0.008 0.000 LATT 1 SYMM 0.5-X, 0.5+Y, 0.5-Z SFAC C H N O CL UNIT 60 60 4 12 8 TEMP -123 L.S. 8 BOND $H CONF FMAP 2 PLAN 5 ACTA 50 REM colourless block SIZE 0.40 0.30 0.30 HTAB O2 O1 HTAB O2 O4_$1 EQIV $1 x-1, y, z REM EXTI 0.000000 WGHT 0.034200 0.616800 FVAR 0.57892 CL2 5 0.043584 0.170386 0.091792 11.00000 0.02707 0.02969 = 0.03375 -0.00089 0.01462 -0.00252 O4 4 0.684497 0.048045 0.402942 11.00000 0.01937 0.02649 = 0.04127 0.00199 0.00809 0.00235 CL1 5 -0.050520 -0.041150 0.155331 11.00000 0.02913 0.01808 = 0.05278 -0.00189 0.00447 0.00063 C7 1 -0.051360 0.105044 0.172907 11.00000 0.02319 0.01650 = 0.03541 0.00190 0.01312 -0.00077 O1 4 -0.261572 0.195566 0.211799 11.00000 0.02781 0.04010 = 0.03550 -0.00011 0.01216 0.00902 O2 4 -0.029428 0.080079 0.347671 11.00000 0.02312 0.05068 = 0.03872 0.01319 0.01393 0.00521 C11 1 0.419880 -0.021644 0.368889 11.00000 0.02530 0.02057 = 0.03271 0.00477 0.00914 0.00263 AFIX 43 H11A 2 0.454379 -0.094867 0.387540 11.00000 -1.20000 AFIX 0 N 3 -0.473727 0.171475 0.017328 11.00000 0.02077 0.03487 = 0.03731 0.01085 0.00839 -0.00196 C14 1 0.317545 0.191229 0.315094 11.00000 0.02607 0.01920 = 0.03207 -0.00034 0.01002 0.00202 AFIX 43 H14A 2 0.283199 0.264650 0.297203 11.00000 -1.20000 AFIX 0 C12 1 0.526817 0.062142 0.372175 11.00000 0.02003 0.02594 = 0.02422 -0.00094 0.00800 0.00079 C6 1 -0.222724 0.147960 0.145490 11.00000 0.02266 0.02211 = 0.03319 0.00482 0.01075 -0.00031 C9 1 0.208643 0.107868 0.310240 11.00000 0.02105 0.02608 = 0.02517 -0.00034 0.00942 0.00126 C10 1 0.262468 0.002131 0.338240 11.00000 0.02397 0.02440 = 0.03580 0.00433 0.01026 -0.00207 AFIX 43 H10A 2 0.189698 -0.055508 0.336391 11.00000 -1.20000 AFIX 0 C15 1 0.740523 -0.062368 0.424445 11.00000 0.02641 0.03064 = 0.04283 0.00349 0.00799 0.00844 AFIX 137 H15A 2 0.854138 -0.061391 0.449919 11.00000 -1.50000 H15B 2 0.709721 -0.106876 0.363659 11.00000 -1.50000 H15C 2 0.696148 -0.094584 0.474509 11.00000 -1.50000 AFIX 0 C8 1 0.037564 0.135126 0.281049 11.00000 0.02168 0.02536 = 0.03101 0.00216 0.01081 0.00160 AFIX 13 H8A 2 0.026595 0.216533 0.289678 11.00000 -1.20000 AFIX 0 C13 1 0.474891 0.168666 0.345572 11.00000 0.02378 0.02189 = 0.03528 -0.00124 0.00961 -0.00382 AFIX 43 H13A 2 0.547772 0.226449 0.348295 11.00000 -1.20000 AFIX 0 C4 1 -0.298112 0.074948 -0.033601 11.00000 0.03344 0.02729 = 0.03757 0.00156 0.01114 -0.00416 AFIX 43 H4A 2 -0.204711 0.039141 -0.035589 11.00000 -1.20000 AFIX 0 C3 1 -0.434536 0.079627 -0.110775 11.00000 0.04399 0.03754 = 0.03327 0.00287 0.00698 -0.01241 AFIX 43 H3A 2 -0.452152 0.047385 -0.174751 11.00000 -1.20000 AFIX 0 C5 1 -0.321745 0.131785 0.047243 11.00000 0.02208 0.02314 = 0.03596 0.00533 0.00999 -0.00210 C1 1 -0.556335 0.234366 0.075295 11.00000 0.02054 0.05199 = 0.04917 0.01042 0.01239 0.00683 AFIX 137 H1A 2 -0.656231 0.259614 0.031753 11.00000 -1.50000 H1B 2 -0.493782 0.298503 0.105319 11.00000 -1.50000 H1C 2 -0.574505 0.187242 0.127765 11.00000 -1.50000 AFIX 0 C2 1 -0.538883 0.139625 -0.077029 11.00000 0.02723 0.04470 = 0.03871 0.01370 0.00197 -0.00955 AFIX 43 H2A 2 -0.642177 0.156294 -0.114773 11.00000 -1.20000 AFIX 0 H2 2 -0.121763 0.103024 0.338064 11.00000 0.05620 HKLF 4 REM mjh76 in P2(1)/n REM R1 = 0.0369 for 2539 Fo > 4sig(Fo) and 0.0509 for all 3145 data REM 196 parameters refined using 0 restraints END ; data_mjh75_3f _database_code_depnum_ccdc_archive 'CCDC 916098' #TrackingRef '16272_web_deposit_cif_file_0_BillClegg_1355797042.mjh.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H12 Cl2 N2 O4' _chemical_formula_sum 'C14 H12 Cl2 N2 O4' _chemical_formula_weight 343.16 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' 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 8.4490(5) _cell_length_b 21.9722(12) _cell_length_c 8.5158(6) _cell_angle_alpha 90.00 _cell_angle_beta 112.479(7) _cell_angle_gamma 90.00 _cell_volume 1460.78(16) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3678 _cell_measurement_theta_min 3.0277 _cell_measurement_theta_max 28.5309 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.560 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 0.464 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.840 _exptl_absorpt_correction_T_max 0.875 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube with Enhance optics' _diffrn_radiation_monochromator none _diffrn_measurement_device_type 'Oxford Diffraction Gemini A Ultra diffractometer' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3968 _diffrn_reflns_number 9235 _diffrn_reflns_av_R_equivalents 0.0288 _diffrn_reflns_av_sigmaI/netI 0.0342 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.03 _diffrn_reflns_theta_max 28.59 _reflns_number_total 3125 _reflns_number_gt 2589 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL and local programs' _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^)+(0.0233P)^2^+0.7057P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0018(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3125 _refine_ls_number_parameters 205 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0467 _refine_ls_R_factor_gt 0.0335 _refine_ls_wR_factor_ref 0.0753 _refine_ls_wR_factor_gt 0.0681 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.12458(5) 0.38070(2) 0.49321(5) 0.02499(13) Uani 1 1 d . . . Cl2 Cl 0.02398(5) 0.46383(2) 0.70320(6) 0.02658(13) Uani 1 1 d . . . N1 N 0.60443(17) 0.43446(7) 0.93114(19) 0.0223(3) Uani 1 1 d . . . N2 N -0.64083(19) 0.28722(8) 0.2368(2) 0.0283(4) Uani 1 1 d . . . O1 O 0.34572(15) 0.35509(7) 0.94600(18) 0.0377(4) Uani 1 1 d . . . O2 O -0.00284(16) 0.35250(7) 0.89104(17) 0.0319(3) Uani 1 1 d . . . H2 H 0.092(3) 0.3453(11) 0.980(3) 0.054(7) Uiso 1 1 d . . . O3 O -0.75967(15) 0.32090(7) 0.22784(17) 0.0395(4) Uani 1 1 d . . . O4 O -0.65717(18) 0.24318(7) 0.1451(2) 0.0431(4) Uani 1 1 d . . . C1 C 0.6877(2) 0.39261(9) 1.0719(3) 0.0302(5) Uani 1 1 d . . . H1A H 0.8104 0.4019 1.1237 0.045 Uiso 1 1 calc R . . H1B H 0.6717 0.3507 1.0294 0.045 Uiso 1 1 calc R . . H1C H 0.6368 0.3972 1.1572 0.045 Uiso 1 1 calc R . . C2 C 0.6880(2) 0.47930(9) 0.8871(2) 0.0275(4) Uani 1 1 d . . . H2A H 0.8060 0.4886 0.9442 0.033 Uiso 1 1 calc R . . C3 C 0.5774(2) 0.50956(9) 0.7476(2) 0.0294(4) Uani 1 1 d . . . H3A H 0.6046 0.5430 0.6917 0.035 Uiso 1 1 calc R . . C4 C 0.4180(2) 0.48215(8) 0.7032(2) 0.0266(4) Uani 1 1 d . . . H4A H 0.3161 0.4935 0.6112 0.032 Uiso 1 1 calc R . . C5 C 0.4343(2) 0.43518(8) 0.8173(2) 0.0218(4) Uani 1 1 d . . . C6 C 0.3114(2) 0.39267(8) 0.8331(2) 0.0238(4) Uani 1 1 d . . . C7 C 0.1232(2) 0.39235(8) 0.6998(2) 0.0212(4) Uani 1 1 d . . . C8 C 0.0217(2) 0.33990(8) 0.7396(2) 0.0230(4) Uani 1 1 d . . . H8A H 0.0911 0.3018 0.7570 0.028 Uiso 1 1 calc R . . C9 C -0.1520(2) 0.32816(8) 0.6021(2) 0.0208(4) Uani 1 1 d . . . C10 C -0.1721(2) 0.28208(8) 0.4850(2) 0.0277(4) Uani 1 1 d . . . H10A H -0.0749 0.2596 0.4881 0.033 Uiso 1 1 calc R . . C11 C -0.3321(2) 0.26844(8) 0.3632(3) 0.0279(4) Uani 1 1 d . . . H11A H -0.3460 0.2372 0.2819 0.033 Uiso 1 1 calc R . . C12 C -0.4702(2) 0.30159(8) 0.3637(2) 0.0221(4) Uani 1 1 d . . . C13 C -0.4550(2) 0.34719(8) 0.4790(2) 0.0221(4) Uani 1 1 d . . . H13A H -0.5529 0.3691 0.4763 0.027 Uiso 1 1 calc R . . C14 C -0.2944(2) 0.36049(8) 0.5989(2) 0.0217(4) Uani 1 1 d . . . H14A H -0.2814 0.3919 0.6796 0.026 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0217(2) 0.0332(3) 0.0209(2) -0.00057(18) 0.00909(17) 0.00017(17) Cl2 0.0231(2) 0.0264(3) 0.0297(3) -0.00104(18) 0.00946(18) 0.00372(17) N1 0.0196(7) 0.0255(8) 0.0215(8) -0.0040(6) 0.0075(6) -0.0018(6) N2 0.0245(8) 0.0381(10) 0.0214(8) 0.0020(7) 0.0079(7) -0.0083(7) O1 0.0215(6) 0.0504(9) 0.0336(8) 0.0195(7) 0.0020(6) -0.0051(6) O2 0.0204(6) 0.0524(9) 0.0215(7) 0.0050(6) 0.0065(6) -0.0021(6) O3 0.0201(6) 0.0709(11) 0.0235(8) -0.0067(7) 0.0037(6) 0.0057(7) O4 0.0399(8) 0.0380(9) 0.0439(9) -0.0153(7) 0.0075(7) -0.0144(7) C1 0.0220(9) 0.0355(11) 0.0288(11) 0.0008(8) 0.0048(8) -0.0001(8) C2 0.0234(9) 0.0313(11) 0.0295(10) -0.0087(8) 0.0120(8) -0.0076(8) C3 0.0341(10) 0.0271(11) 0.0318(11) -0.0016(8) 0.0179(9) -0.0058(8) C4 0.0266(9) 0.0268(10) 0.0272(10) 0.0000(8) 0.0113(8) 0.0017(7) C5 0.0185(8) 0.0262(10) 0.0205(9) -0.0023(7) 0.0075(7) 0.0005(7) C6 0.0190(8) 0.0291(10) 0.0225(10) 0.0021(8) 0.0072(7) 0.0013(7) C7 0.0186(8) 0.0257(10) 0.0195(9) 0.0027(7) 0.0076(7) 0.0031(7) C8 0.0174(8) 0.0278(10) 0.0234(10) 0.0036(7) 0.0073(7) 0.0018(7) C9 0.0180(8) 0.0215(9) 0.0237(9) 0.0033(7) 0.0088(7) 0.0008(7) C10 0.0223(9) 0.0242(10) 0.0385(12) -0.0013(8) 0.0137(8) 0.0029(7) C11 0.0300(9) 0.0239(10) 0.0323(11) -0.0068(8) 0.0149(8) -0.0037(8) C12 0.0202(8) 0.0254(10) 0.0201(9) 0.0015(7) 0.0068(7) -0.0052(7) C13 0.0184(8) 0.0265(10) 0.0234(9) 0.0038(7) 0.0101(7) 0.0024(7) C14 0.0212(8) 0.0242(10) 0.0203(9) -0.0014(7) 0.0087(7) 0.0004(7) _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 C7 1.7824(18) . ? Cl2 C7 1.7859(18) . ? N1 C1 1.460(2) . ? N1 C2 1.346(2) . ? N1 C5 1.393(2) . ? N2 O3 1.226(2) . ? N2 O4 1.218(2) . ? N2 C12 1.468(2) . ? O1 C6 1.215(2) . ? O2 H2 0.88(3) . ? O2 C8 1.409(2) . ? C1 H1A 0.980 . ? C1 H1B 0.980 . ? C1 H1C 0.980 . ? C2 H2A 0.950 . ? C2 C3 1.370(3) . ? C3 H3A 0.950 . ? C3 C4 1.389(2) . ? C4 H4A 0.950 . ? C4 C5 1.387(3) . ? C5 C6 1.441(2) . ? C6 C7 1.560(2) . ? C7 C8 1.550(2) . ? C8 H8A 1.000 . ? C8 C9 1.509(2) . ? C9 C10 1.385(3) . ? C9 C14 1.388(2) . ? C10 H10A 0.950 . ? C10 C11 1.386(2) . ? C11 H11A 0.950 . ? C11 C12 1.377(2) . ? C12 C13 1.374(3) . ? C13 H13A 0.950 . ? C13 C14 1.382(2) . ? C14 H14A 0.950 . ? 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 C1 N1 C2 123.39(14) . . ? C1 N1 C5 128.57(15) . . ? C2 N1 C5 108.01(15) . . ? O3 N2 O4 123.40(16) . . ? O3 N2 C12 117.77(16) . . ? O4 N2 C12 118.82(16) . . ? H2 O2 C8 110.2(17) . . ? N1 C1 H1A 109.5 . . ? N1 C1 H1B 109.5 . . ? N1 C1 H1C 109.5 . . ? H1A C1 H1B 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 H2A 125.0 . . ? N1 C2 C3 109.91(15) . . ? H2A C2 C3 125.0 . . ? C2 C3 H3A 126.5 . . ? C2 C3 C4 107.09(17) . . ? H3A C3 C4 126.5 . . ? C3 C4 H4A 126.1 . . ? C3 C4 C5 107.81(16) . . ? H4A C4 C5 126.1 . . ? N1 C5 C4 107.17(15) . . ? N1 C5 C6 121.09(16) . . ? C4 C5 C6 131.73(16) . . ? O1 C6 C5 123.48(16) . . ? O1 C6 C7 116.17(15) . . ? C5 C6 C7 120.34(15) . . ? Cl1 C7 Cl2 108.81(9) . . ? Cl1 C7 C6 109.24(12) . . ? Cl1 C7 C8 108.80(12) . . ? Cl2 C7 C6 109.77(12) . . ? Cl2 C7 C8 110.36(12) . . ? C6 C7 C8 109.84(14) . . ? O2 C8 C7 109.96(15) . . ? O2 C8 H8A 108.2 . . ? O2 C8 C9 107.69(14) . . ? C7 C8 H8A 108.2 . . ? C7 C8 C9 114.38(15) . . ? H8A C8 C9 108.2 . . ? C8 C9 C10 119.90(15) . . ? C8 C9 C14 120.39(16) . . ? C10 C9 C14 119.57(15) . . ? C9 C10 H10A 119.6 . . ? C9 C10 C11 120.83(16) . . ? H10A C10 C11 119.6 . . ? C10 C11 H11A 121.0 . . ? C10 C11 C12 117.95(17) . . ? H11A C11 C12 121.0 . . ? N2 C12 C11 118.59(16) . . ? N2 C12 C13 118.72(16) . . ? C11 C12 C13 122.69(16) . . ? C12 C13 H13A 120.7 . . ? C12 C13 C14 118.64(16) . . ? H13A C13 C14 120.7 . . ? C9 C14 C13 120.32(17) . . ? C9 C14 H14A 119.8 . . ? C13 C14 H14A 119.8 . . ? 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 C1 N1 C2 C3 178.11(17) . . . . ? C5 N1 C2 C3 0.1(2) . . . . ? N1 C2 C3 C4 0.0(2) . . . . ? C2 C3 C4 C5 -0.1(2) . . . . ? C3 C4 C5 N1 0.2(2) . . . . ? C3 C4 C5 C6 178.97(19) . . . . ? C1 N1 C5 C4 -178.03(17) . . . . ? C1 N1 C5 C6 3.0(3) . . . . ? C2 N1 C5 C4 -0.2(2) . . . . ? C2 N1 C5 C6 -179.13(16) . . . . ? N1 C5 C6 O1 1.6(3) . . . . ? N1 C5 C6 C7 -177.39(15) . . . . ? C4 C5 C6 O1 -177.1(2) . . . . ? C4 C5 C6 C7 4.0(3) . . . . ? O1 C6 C7 Cl1 -121.94(17) . . . . ? O1 C6 C7 Cl2 118.83(17) . . . . ? O1 C6 C7 C8 -2.7(2) . . . . ? C5 C6 C7 Cl1 57.1(2) . . . . ? C5 C6 C7 Cl2 -62.13(19) . . . . ? C5 C6 C7 C8 176.35(16) . . . . ? Cl1 C7 C8 O2 -171.48(11) . . . . ? Cl1 C7 C8 C9 -50.18(18) . . . . ? Cl2 C7 C8 O2 -52.17(16) . . . . ? Cl2 C7 C8 C9 69.13(18) . . . . ? C6 C7 C8 O2 69.00(18) . . . . ? C6 C7 C8 C9 -169.70(14) . . . . ? O2 C8 C9 C10 -139.77(17) . . . . ? O2 C8 C9 C14 35.9(2) . . . . ? C7 C8 C9 C10 97.7(2) . . . . ? C7 C8 C9 C14 -86.7(2) . . . . ? C8 C9 C10 C11 176.59(17) . . . . ? C14 C9 C10 C11 0.9(3) . . . . ? C9 C10 C11 C12 -0.7(3) . . . . ? C10 C11 C12 N2 -179.32(16) . . . . ? C10 C11 C12 C13 0.2(3) . . . . ? O3 N2 C12 C11 -172.91(17) . . . . ? O3 N2 C12 C13 7.6(2) . . . . ? O4 N2 C12 C11 6.4(3) . . . . ? O4 N2 C12 C13 -173.10(17) . . . . ? N2 C12 C13 C14 179.73(15) . . . . ? C11 C12 C13 C14 0.2(3) . . . . ? C12 C13 C14 C9 -0.1(3) . . . . ? C8 C9 C14 C13 -176.15(16) . . . . ? C10 C9 C14 C13 -0.5(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H2 O3 0.88(3) 2.07(3) 2.9023(19) 157(2) 1_656 O2 H2 O1 0.88(3) 2.28(2) 2.8002(18) 118(2) . _diffrn_measured_fraction_theta_max 0.834 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.305 _refine_diff_density_min -0.237 _refine_diff_density_rms 0.052 # Contents of RES file _computing_special_details ; TITL mjh75 in P2(1)/c CELL 0.71073 8.4490 21.9722 8.5158 90.000 112.479 90.000 ZERR 4.00 0.0005 0.0012 0.0006 0.000 0.007 0.000 LATT 1 SYMM -X, 0.5+Y, 0.5-Z SFAC C H N O CL UNIT 56 48 8 16 8 TEMP -123 SIZE 0.30 0.30 0.20 L.S. 8 BOND $H CONF FMAP 2 PLAN 5 HTAB O2 O3_$1 EQIV $1 x+1, y, z+1 HTAB O2 O1 ACTA 50 WGHT 0.023300 0.705700 EXTI 0.001845 FVAR 0.71085 CL1 5 0.124584 0.380698 0.493212 11.00000 0.02169 0.03318 = 0.02095 -0.00057 0.00909 0.00017 CL2 5 0.023977 0.463829 0.703201 11.00000 0.02307 0.02638 = 0.02973 -0.00104 0.00946 0.00372 N1 3 0.604429 0.434464 0.931138 11.00000 0.01955 0.02547 = 0.02153 -0.00396 0.00751 -0.00180 N2 3 -0.640831 0.287221 0.236762 11.00000 0.02448 0.03814 = 0.02144 0.00205 0.00787 -0.00831 O1 4 0.345717 0.355090 0.946003 11.00000 0.02146 0.05044 = 0.03364 0.01954 0.00198 -0.00511 O2 4 -0.002843 0.352503 0.891043 11.00000 0.02045 0.05239 = 0.02152 0.00497 0.00653 -0.00206 H2 2 0.092014 0.345349 0.979581 11.00000 0.05413 O3 4 -0.759672 0.320903 0.227845 11.00000 0.02006 0.07092 = 0.02350 -0.00668 0.00374 0.00566 O4 4 -0.657174 0.243184 0.145081 11.00000 0.03991 0.03796 = 0.04385 -0.01531 0.00753 -0.01441 C1 1 0.687683 0.392612 1.071904 11.00000 0.02202 0.03548 = 0.02884 0.00081 0.00481 -0.00009 AFIX 137 H1A 2 0.810353 0.401857 1.123664 11.00000 -1.50000 H1B 2 0.671739 0.350694 1.029355 11.00000 -1.50000 H1C 2 0.636829 0.397199 1.157158 11.00000 -1.50000 AFIX 0 C2 1 0.687967 0.479299 0.887080 11.00000 0.02343 0.03134 = 0.02949 -0.00872 0.01205 -0.00761 AFIX 43 H2A 2 0.806047 0.488583 0.944232 11.00000 -1.20000 AFIX 0 C3 1 0.577419 0.509558 0.747571 11.00000 0.03407 0.02712 = 0.03181 -0.00162 0.01794 -0.00577 AFIX 43 H3A 2 0.604638 0.542985 0.691688 11.00000 -1.20000 AFIX 0 C4 1 0.418038 0.482151 0.703235 11.00000 0.02657 0.02683 = 0.02718 0.00002 0.01128 0.00173 AFIX 43 H4A 2 0.316074 0.493543 0.611235 11.00000 -1.20000 AFIX 0 C5 1 0.434306 0.435176 0.817259 11.00000 0.01852 0.02623 = 0.02055 -0.00234 0.00752 0.00046 C6 1 0.311350 0.392670 0.833104 11.00000 0.01899 0.02915 = 0.02253 0.00205 0.00719 0.00129 C7 1 0.123237 0.392346 0.699839 11.00000 0.01862 0.02570 = 0.01951 0.00272 0.00763 0.00308 C8 1 0.021697 0.339900 0.739647 11.00000 0.01737 0.02776 = 0.02336 0.00363 0.00728 0.00177 AFIX 13 H8A 2 0.091060 0.301798 0.756958 11.00000 -1.20000 AFIX 0 C9 1 -0.152048 0.328157 0.602107 11.00000 0.01803 0.02148 = 0.02371 0.00331 0.00880 0.00084 C10 1 -0.172091 0.282081 0.484963 11.00000 0.02234 0.02419 = 0.03849 -0.00134 0.01367 0.00294 AFIX 43 H10A 2 -0.074933 0.259557 0.488147 11.00000 -1.20000 AFIX 0 C11 1 -0.332081 0.268439 0.363210 11.00000 0.03001 0.02390 = 0.03232 -0.00682 0.01489 -0.00368 AFIX 43 H11A 2 -0.346039 0.237186 0.281895 11.00000 -1.20000 AFIX 0 C12 1 -0.470248 0.301594 0.363732 11.00000 0.02015 0.02536 = 0.02006 0.00148 0.00683 -0.00521 C13 1 -0.455032 0.347193 0.478986 11.00000 0.01840 0.02648 = 0.02337 0.00383 0.01005 0.00239 AFIX 43 H13A 2 -0.552912 0.369138 0.476310 11.00000 -1.20000 AFIX 0 C14 1 -0.294403 0.360492 0.598923 11.00000 0.02121 0.02423 = 0.02030 -0.00143 0.00873 0.00040 AFIX 43 H14A 2 -0.281354 0.391912 0.679569 11.00000 -1.20000 HKLF 4 REM mjh75 in P2(1)/c REM R1 = 0.0335 for 2589 Fo > 4sig(Fo) and 0.0467 for all 3125 data REM 205 parameters refined using 0 restraints END ; data_mjh79_3g _database_code_depnum_ccdc_archive 'CCDC 916099' #TrackingRef '16272_web_deposit_cif_file_0_BillClegg_1355797042.mjh.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H12 Cl2 N2 O3' _chemical_formula_sum 'C14 H12 Cl2 N2 O3' _chemical_formula_weight 327.16 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' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.8490(11) _cell_length_b 8.8572(6) _cell_length_c 9.6786(9) _cell_angle_alpha 88.060(6) _cell_angle_beta 72.636(10) _cell_angle_gamma 80.267(8) _cell_volume 713.48(12) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2302 _cell_measurement_theta_min 3.08 _cell_measurement_theta_max 28.67 _exptl_crystal_description slab _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.523 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 336 _exptl_absorpt_coefficient_mu 0.466 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.873 _exptl_absorpt_correction_T_max 0.955 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube with Enhance optics' _diffrn_radiation_monochromator none _diffrn_measurement_device_type 'Oxford Diffraction Gemini A Ultra diffractometer' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3968 _diffrn_reflns_number 5166 _diffrn_reflns_av_R_equivalents 0.0211 _diffrn_reflns_av_sigmaI/netI 0.0369 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.09 _diffrn_reflns_theta_max 28.73 _reflns_number_total 2967 _reflns_number_gt 2526 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL and local programs' _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^)+(0.0249P)^2^+0.3136P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2967 _refine_ls_number_parameters 210 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0422 _refine_ls_R_factor_gt 0.0331 _refine_ls_wR_factor_ref 0.0768 _refine_ls_wR_factor_gt 0.0711 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _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 -0.05490(5) 0.28680(5) 0.99107(5) 0.02487(12) Uani 1 1 d . . . Cl2 Cl 0.18045(5) 0.07567(4) 0.77599(5) 0.02435(12) Uani 1 1 d . . . N1 N 0.40970(17) 0.19442(16) 1.10096(15) 0.0206(3) Uani 1 1 d . . . N2 N -0.3412(2) 0.29794(19) 0.45195(18) 0.0327(4) Uani 1 1 d . . . O1 O 0.34112(16) 0.39016(14) 0.87719(14) 0.0294(3) Uani 1 1 d . . . O2 O -0.297(2) 0.239(2) 0.340(3) 0.056(4) Uani 0.42(6) 1 d P A 1 O3 O -0.4839(8) 0.358(4) 0.5092(14) 0.057(4) Uani 0.58(6) 1 d P A 1 O2A O -0.2938(12) 0.2536(15) 0.3226(13) 0.035(2) Uani 0.58(6) 1 d P A 2 O3A O -0.4757(18) 0.283(4) 0.5301(13) 0.051(4) Uani 0.42(6) 1 d P A 2 C1 C 0.5315(2) 0.2937(2) 1.0627(2) 0.0287(4) Uani 1 1 d . . . H1A H 0.6046 0.2685 1.1219 0.043 Uiso 1 1 calc R . . H1B H 0.4792 0.4009 1.0804 0.043 Uiso 1 1 calc R . . H1C H 0.5923 0.2783 0.9600 0.043 Uiso 1 1 calc R . . C2 C 0.4025(2) 0.0883(2) 1.20500(19) 0.0270(4) Uani 1 1 d . . . H2A H 0.4715 0.0708 1.2646 0.032 Uiso 1 1 calc R . . C3 C 0.2797(2) 0.0092(2) 1.2112(2) 0.0289(4) Uani 1 1 d . . . H3A H 0.2487 -0.0711 1.2755 0.035 Uiso 1 1 calc R . . C4 C 0.2095(2) 0.06849(19) 1.10611(19) 0.0245(4) Uani 1 1 d . . . H4A H 0.1220 0.0355 1.0849 0.029 Uiso 1 1 calc R . . C5 C 0.2905(2) 0.18525(18) 1.03724(18) 0.0194(3) Uani 1 1 d . . . C6 C 0.2659(2) 0.28678(18) 0.92238(18) 0.0193(4) Uani 1 1 d . . . C7 C 0.1339(2) 0.26537(18) 0.85226(18) 0.0191(3) Uani 1 1 d . . . C8 C 0.1240(2) 0.38215(19) 0.73397(19) 0.0218(4) Uani 1 1 d . . . H8A H 0.0978 0.4864 0.7776 0.026 Uiso 1 1 calc R . . H8B H 0.2309 0.3731 0.6608 0.026 Uiso 1 1 calc R . . C9 C 0.0013(2) 0.36383(18) 0.65867(18) 0.0204(4) Uani 1 1 d . . . C10 C -0.1588(2) 0.4327(2) 0.71373(19) 0.0252(4) Uani 1 1 d . A . H10A H -0.1905 0.4956 0.7985 0.030 Uiso 1 1 calc R . . C11 C -0.2725(2) 0.4114(2) 0.64752(19) 0.0272(4) Uani 1 1 d . . . H11A H -0.3820 0.4560 0.6873 0.033 Uiso 1 1 calc R A . C12 C -0.2221(2) 0.3236(2) 0.52235(19) 0.0236(4) Uani 1 1 d . A . C13 C -0.0645(2) 0.2571(2) 0.46146(19) 0.0253(4) Uani 1 1 d . . . H13A H -0.0329 0.1989 0.3739 0.030 Uiso 1 1 calc R A . C14 C 0.0467(2) 0.2772(2) 0.53085(19) 0.0250(4) Uani 1 1 d . A . H14A H 0.1558 0.2312 0.4908 0.030 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0147(2) 0.0333(2) 0.0261(2) -0.00174(17) -0.00435(17) -0.00508(16) Cl2 0.0248(2) 0.0218(2) 0.0294(2) -0.00541(16) -0.01165(18) -0.00398(16) N1 0.0149(7) 0.0255(7) 0.0224(8) -0.0010(6) -0.0072(6) -0.0029(6) N2 0.0324(10) 0.0426(10) 0.0297(10) -0.0005(8) -0.0170(8) -0.0104(8) O1 0.0270(7) 0.0308(7) 0.0389(8) 0.0091(6) -0.0174(6) -0.0165(6) O2 0.074(8) 0.052(6) 0.050(7) -0.035(6) -0.046(6) 0.024(5) O3 0.0224(18) 0.110(11) 0.042(3) -0.018(4) -0.0135(17) -0.007(3) O2A 0.036(4) 0.050(3) 0.025(3) 0.000(3) -0.017(2) -0.012(3) O3A 0.027(3) 0.089(11) 0.043(3) -0.005(5) -0.013(2) -0.024(4) C1 0.0210(10) 0.0408(11) 0.0310(10) 0.0023(8) -0.0137(8) -0.0130(8) C2 0.0230(10) 0.0339(10) 0.0235(10) 0.0002(7) -0.0092(8) 0.0012(8) C3 0.0303(11) 0.0265(9) 0.0273(10) 0.0050(7) -0.0061(8) -0.0032(8) C4 0.0216(10) 0.0248(9) 0.0279(10) -0.0009(7) -0.0067(8) -0.0072(7) C5 0.0157(9) 0.0218(8) 0.0215(9) -0.0034(6) -0.0061(7) -0.0034(6) C6 0.0146(8) 0.0209(8) 0.0230(9) -0.0037(7) -0.0054(7) -0.0042(6) C7 0.0138(8) 0.0211(8) 0.0226(9) -0.0035(6) -0.0045(7) -0.0046(6) C8 0.0194(9) 0.0243(9) 0.0239(9) 0.0014(7) -0.0082(7) -0.0066(7) C9 0.0201(9) 0.0216(8) 0.0217(9) 0.0034(7) -0.0086(7) -0.0060(7) C10 0.0235(10) 0.0298(9) 0.0233(9) -0.0056(7) -0.0101(8) -0.0004(7) C11 0.0191(10) 0.0375(10) 0.0241(10) -0.0029(8) -0.0068(8) -0.0006(7) C12 0.0234(10) 0.0292(9) 0.0221(9) 0.0029(7) -0.0108(7) -0.0082(7) C13 0.0298(10) 0.0276(9) 0.0186(9) -0.0027(7) -0.0084(8) -0.0025(7) C14 0.0209(9) 0.0307(10) 0.0212(9) 0.0004(7) -0.0049(7) -0.0007(7) _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 C7 1.7893(17) . ? Cl2 C7 1.7906(16) . ? N1 C1 1.460(2) . ? N1 C2 1.349(2) . ? N1 C5 1.386(2) . ? N2 O2 1.149(18) . ? N2 O3 1.249(8) . ? N2 O2A 1.249(11) . ? N2 O3A 1.231(9) . ? N2 C12 1.465(2) . ? O1 C6 1.216(2) . ? C1 H1A 0.980 . ? C1 H1B 0.980 . ? C1 H1C 0.980 . ? C2 H2A 0.950 . ? C2 C3 1.375(3) . ? C3 H3A 0.950 . ? C3 C4 1.388(3) . ? C4 H4A 0.950 . ? C4 C5 1.395(2) . ? C5 C6 1.450(2) . ? C6 C7 1.555(2) . ? C7 C8 1.529(2) . ? C8 H8A 0.990 . ? C8 H8B 0.990 . ? C8 C9 1.509(2) . ? C9 C10 1.393(2) . ? C9 C14 1.394(2) . ? C10 H10A 0.950 . ? C10 C11 1.384(3) . ? C11 H11A 0.950 . ? C11 C12 1.377(3) . ? C12 C13 1.376(3) . ? C13 H13A 0.950 . ? C13 C14 1.383(3) . ? C14 H14A 0.950 . ? 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 C1 N1 C2 123.13(15) . . ? C1 N1 C5 128.16(14) . . ? C2 N1 C5 108.64(14) . . ? O2 N2 O3 122.9(10) . . ? O2 N2 C12 118.8(9) . . ? O3 N2 C12 117.8(5) . . ? O2A N2 O3A 120.9(6) . . ? O2A N2 C12 118.8(5) . . ? O3A N2 C12 117.7(6) . . ? N1 C1 H1A 109.5 . . ? N1 C1 H1B 109.5 . . ? N1 C1 H1C 109.5 . . ? H1A C1 H1B 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 H2A 125.3 . . ? N1 C2 C3 109.35(17) . . ? H2A C2 C3 125.3 . . ? C2 C3 H3A 126.3 . . ? C2 C3 C4 107.30(16) . . ? H3A C3 C4 126.3 . . ? C3 C4 H4A 126.1 . . ? C3 C4 C5 107.72(16) . . ? H4A C4 C5 126.1 . . ? N1 C5 C4 106.98(15) . . ? N1 C5 C6 121.81(14) . . ? C4 C5 C6 131.20(16) . . ? O1 C6 C5 124.24(16) . . ? O1 C6 C7 116.97(15) . . ? C5 C6 C7 118.78(14) . . ? Cl1 C7 Cl2 109.31(8) . . ? Cl1 C7 C6 108.36(11) . . ? Cl1 C7 C8 109.56(12) . . ? Cl2 C7 C6 108.29(11) . . ? Cl2 C7 C8 109.51(12) . . ? C6 C7 C8 111.76(13) . . ? C7 C8 H8A 108.7 . . ? C7 C8 H8B 108.7 . . ? C7 C8 C9 114.16(14) . . ? H8A C8 H8B 107.6 . . ? H8A C8 C9 108.7 . . ? H8B C8 C9 108.7 . . ? C8 C9 C10 121.38(15) . . ? C8 C9 C14 120.23(16) . . ? C10 C9 C14 118.39(16) . . ? C9 C10 H10A 119.3 . . ? C9 C10 C11 121.36(16) . . ? H10A C10 C11 119.3 . . ? C10 C11 H11A 121.0 . . ? C10 C11 C12 118.04(17) . . ? H11A C11 C12 121.0 . . ? N2 C12 C11 118.79(17) . . ? N2 C12 C13 118.51(16) . . ? C11 C12 C13 122.69(17) . . ? C12 C13 H13A 120.8 . . ? C12 C13 C14 118.39(16) . . ? H13A C13 C14 120.8 . . ? C9 C14 C13 121.08(17) . . ? C9 C14 H14A 119.5 . . ? C13 C14 H14A 119.5 . . ? 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 C1 N1 C2 C3 -177.42(16) . . . . ? C5 N1 C2 C3 -0.2(2) . . . . ? N1 C2 C3 C4 0.4(2) . . . . ? C2 C3 C4 C5 -0.5(2) . . . . ? C1 N1 C5 C4 176.92(16) . . . . ? C1 N1 C5 C6 -3.8(3) . . . . ? C2 N1 C5 C4 -0.17(19) . . . . ? C2 N1 C5 C6 179.08(15) . . . . ? C3 C4 C5 N1 0.43(19) . . . . ? C3 C4 C5 C6 -178.71(17) . . . . ? N1 C5 C6 O1 -3.1(3) . . . . ? N1 C5 C6 C7 177.70(14) . . . . ? C4 C5 C6 O1 175.93(18) . . . . ? C4 C5 C6 C7 -3.3(3) . . . . ? O1 C6 C7 Cl1 -120.30(15) . . . . ? O1 C6 C7 Cl2 121.22(14) . . . . ? O1 C6 C7 C8 0.5(2) . . . . ? C5 C6 C7 Cl1 58.95(17) . . . . ? C5 C6 C7 Cl2 -59.52(17) . . . . ? C5 C6 C7 C8 179.77(14) . . . . ? Cl1 C7 C8 C9 -61.68(17) . . . . ? Cl2 C7 C8 C9 58.20(17) . . . . ? C6 C7 C8 C9 178.20(14) . . . . ? C7 C8 C9 C10 86.50(19) . . . . ? C7 C8 C9 C14 -93.80(19) . . . . ? C8 C9 C10 C11 -177.64(16) . . . . ? C14 C9 C10 C11 2.7(3) . . . . ? C9 C10 C11 C12 -2.0(3) . . . . ? C10 C11 C12 N2 179.12(16) . . . . ? C10 C11 C12 C13 0.0(3) . . . . ? O2 N2 C12 C11 171.8(15) . . . . ? O2 N2 C12 C13 -9.0(15) . . . . ? O3 N2 C12 C11 0.3(19) . . . . ? O3 N2 C12 C13 179.4(19) . . . . ? O2A N2 C12 C11 161.9(7) . . . . ? O2A N2 C12 C13 -18.9(7) . . . . ? O3A N2 C12 C11 -36(2) . . . . ? O3A N2 C12 C13 143(2) . . . . ? N2 C12 C13 C14 -177.82(15) . . . . ? C11 C12 C13 C14 1.3(3) . . . . ? C12 C13 C14 C9 -0.6(3) . . . . ? C8 C9 C14 C13 179.00(15) . . . . ? C10 C9 C14 C13 -1.3(2) . . . . ? _diffrn_measured_fraction_theta_max 0.806 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.337 _refine_diff_density_min -0.295 _refine_diff_density_rms 0.054 # Contents of RES file _computing_special_details ; TITL mjh79 in P-1 CELL 0.71073 8.8490 8.8572 9.6786 88.060 72.636 80.267 ZERR 2.00 0.0011 0.0006 0.0009 0.006 0.010 0.008 LATT 1 SFAC C H N O CL UNIT 28 24 4 6 4 TEMP -123 L.S. 8 LIST 1 FMAP 2 PLAN 5 ACTA 50 BOND $H CONF REM colourless slab SIZE 0.30 0.30 0.10 REM EXTI 0.003834 WGHT 0.024900 0.313600 FVAR 0.32778 0.57907 CL1 5 -0.054903 0.286801 0.991070 11.00000 0.01467 0.03327 = 0.02611 -0.00174 -0.00435 -0.00508 CL2 5 0.180452 0.075665 0.775987 11.00000 0.02476 0.02175 = 0.02937 -0.00541 -0.01165 -0.00398 N1 3 0.409705 0.194421 1.100964 11.00000 0.01491 0.02553 = 0.02240 -0.00096 -0.00722 -0.00291 N2 3 -0.341159 0.297938 0.451947 11.00000 0.03236 0.04265 = 0.02975 -0.00047 -0.01695 -0.01037 O1 4 0.341122 0.390165 0.877189 11.00000 0.02703 0.03082 = 0.03889 0.00908 -0.01738 -0.01651 PART 1 O2 4 -0.297255 0.238774 0.339835 -21.00000 0.07414 0.05187 = 0.05016 -0.03471 -0.04648 0.02377 O3 4 -0.483851 0.357970 0.509151 21.00000 0.02239 0.10983 = 0.04242 -0.01781 -0.01349 -0.00704 PART 2 O2A 4 -0.293768 0.253606 0.322640 21.00000 0.03639 0.04959 = 0.02489 0.00030 -0.01714 -0.01173 O3A 4 -0.475656 0.283031 0.530121 -21.00000 0.02732 0.08890 = 0.04333 -0.00498 -0.01320 -0.02386 PART 0 C1 1 0.531476 0.293703 1.062678 11.00000 0.02102 0.04082 = 0.03102 0.00226 -0.01369 -0.01300 AFIX 137 H1A 2 0.604610 0.268512 1.121854 11.00000 -1.50000 H1B 2 0.479213 0.400923 1.080438 11.00000 -1.50000 H1C 2 0.592338 0.278314 0.960045 11.00000 -1.50000 AFIX 0 C2 1 0.402526 0.088253 1.204998 11.00000 0.02302 0.03390 = 0.02354 0.00021 -0.00920 0.00125 AFIX 43 H2A 2 0.471535 0.070840 1.264644 11.00000 -1.20000 AFIX 0 C3 1 0.279742 0.009211 1.211201 11.00000 0.03032 0.02652 = 0.02730 0.00501 -0.00606 -0.00322 AFIX 43 H3A 2 0.248701 -0.071090 1.275484 11.00000 -1.20000 AFIX 0 C4 1 0.209517 0.068488 1.106114 11.00000 0.02160 0.02479 = 0.02795 -0.00087 -0.00670 -0.00721 AFIX 43 H4A 2 0.122030 0.035462 1.084909 11.00000 -1.20000 AFIX 0 C5 1 0.290472 0.185252 1.037240 11.00000 0.01568 0.02176 = 0.02152 -0.00337 -0.00612 -0.00335 C6 1 0.265868 0.286784 0.922378 11.00000 0.01459 0.02087 = 0.02296 -0.00368 -0.00536 -0.00418 C7 1 0.133856 0.265371 0.852265 11.00000 0.01385 0.02113 = 0.02259 -0.00347 -0.00452 -0.00462 C8 1 0.124036 0.382154 0.733969 11.00000 0.01936 0.02435 = 0.02395 0.00139 -0.00820 -0.00657 AFIX 23 H8A 2 0.097770 0.486417 0.777558 11.00000 -1.20000 H8B 2 0.230870 0.373105 0.660823 11.00000 -1.20000 AFIX 0 C9 1 0.001283 0.363829 0.658669 11.00000 0.02015 0.02157 = 0.02171 0.00344 -0.00863 -0.00604 C10 1 -0.158754 0.432714 0.713727 11.00000 0.02350 0.02977 = 0.02326 -0.00562 -0.01010 -0.00039 AFIX 43 H10A 2 -0.190497 0.495629 0.798460 11.00000 -1.20000 AFIX 0 C11 1 -0.272454 0.411375 0.647516 11.00000 0.01913 0.03750 = 0.02409 -0.00286 -0.00683 -0.00062 AFIX 43 H11A 2 -0.382032 0.455989 0.687282 11.00000 -1.20000 AFIX 0 C12 1 -0.222066 0.323603 0.522353 11.00000 0.02345 0.02918 = 0.02208 0.00295 -0.01082 -0.00820 C13 1 -0.064538 0.257135 0.461459 11.00000 0.02984 0.02765 = 0.01858 -0.00270 -0.00842 -0.00250 AFIX 43 H13A 2 -0.032917 0.198868 0.373871 11.00000 -1.20000 AFIX 0 C14 1 0.046664 0.277201 0.530849 11.00000 0.02088 0.03073 = 0.02124 0.00036 -0.00487 -0.00070 AFIX 43 H14A 2 0.155752 0.231209 0.490769 11.00000 -1.20000 HKLF 4 REM mjh79 in P-1 REM R1 = 0.0331 for 2526 Fo > 4sig(Fo) and 0.0422 for all 2967 data REM 210 parameters refined using 0 restraints END ; data_mjh77_3h _database_code_depnum_ccdc_archive 'CCDC 916100' #TrackingRef '16272_web_deposit_cif_file_0_BillClegg_1355797042.mjh.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 Cl2 N2 O4' _chemical_formula_sum 'C14 H10 Cl2 N2 O4' _chemical_formula_weight 341.14 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 'P b c a' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 12.4615(6) _cell_length_b 13.4977(5) _cell_length_c 17.2015(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2893.3(2) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5529 _cell_measurement_theta_min 3.01 _cell_measurement_theta_max 28.50 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.566 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1392 _exptl_absorpt_coefficient_mu 0.468 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.872 _exptl_absorpt_correction_T_max 0.955 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube with Enhance optics' _diffrn_radiation_monochromator none _diffrn_measurement_device_type 'Oxford Diffraction Gemini A Ultra diffractometer' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3968 _diffrn_reflns_number 13352 _diffrn_reflns_av_R_equivalents 0.0326 _diffrn_reflns_av_sigmaI/netI 0.0296 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.02 _diffrn_reflns_theta_max 28.56 _reflns_number_total 3223 _reflns_number_gt 2709 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL and local programs' _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^)+(0.0258P)^2^+1.7441P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0011(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3223 _refine_ls_number_parameters 201 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0426 _refine_ls_R_factor_gt 0.0323 _refine_ls_wR_factor_ref 0.0753 _refine_ls_wR_factor_gt 0.0693 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _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 0.96530(3) 0.68376(3) 0.49929(2) 0.02529(12) Uani 1 1 d . . . Cl2 Cl 0.86897(4) 0.77442(3) 0.63311(2) 0.02767(12) Uani 1 1 d . . . N1 N 0.80306(11) 0.45779(9) 0.71317(8) 0.0220(3) Uani 1 1 d . . . N3 N 0.63074(13) 0.32619(10) 0.35286(8) 0.0267(3) Uani 1 1 d . . . O1 O 0.97291(9) 0.53449(9) 0.61518(7) 0.0267(3) Uani 1 1 d . . . O2 O 0.69494(9) 0.73649(8) 0.53144(7) 0.0257(3) Uani 1 1 d . . . O3 O 0.53965(11) 0.32316(10) 0.32733(9) 0.0416(4) Uani 1 1 d . . . O4 O 0.69592(11) 0.25930(9) 0.34525(8) 0.0381(3) Uani 1 1 d . . . C1 C 0.88406(16) 0.37973(12) 0.71018(11) 0.0331(4) Uani 1 1 d . . . H1A H 0.8618 0.3245 0.7434 0.050 Uiso 1 1 calc R . . H1B H 0.9529 0.4059 0.7286 0.050 Uiso 1 1 calc R . . H1C H 0.8918 0.3564 0.6565 0.050 Uiso 1 1 calc R . . C2 C 0.71109(15) 0.45094(12) 0.75386(9) 0.0266(4) Uani 1 1 d . . . H2A H 0.6921 0.3972 0.7868 0.032 Uiso 1 1 calc R . . C3 C 0.64886(15) 0.53307(12) 0.74071(10) 0.0267(4) Uani 1 1 d . . . H3A H 0.5805 0.5465 0.7628 0.032 Uiso 1 1 calc R . . C4 C 0.70455(13) 0.59275(11) 0.68908(9) 0.0223(3) Uani 1 1 d . . . H4A H 0.6809 0.6546 0.6691 0.027 Uiso 1 1 calc R . . C5 C 0.80106(13) 0.54619(11) 0.67161(9) 0.0198(3) Uani 1 1 d . . . C6 C 0.88685(13) 0.57611(11) 0.62146(9) 0.0187(3) Uani 1 1 d . . . C7 C 0.86411(13) 0.66990(10) 0.57049(9) 0.0189(3) Uani 1 1 d . . . C8 C 0.75525(13) 0.66758(10) 0.52641(9) 0.0176(3) Uani 1 1 d . . . C9 C 0.72851(12) 0.57725(10) 0.47950(9) 0.0174(3) Uani 1 1 d . . . C10 C 0.62405(13) 0.57198(12) 0.45005(10) 0.0240(4) Uani 1 1 d . . . H10A H 0.5755 0.6251 0.4587 0.029 Uiso 1 1 calc R . . C11 C 0.59111(14) 0.49003(12) 0.40858(10) 0.0247(4) Uani 1 1 d . . . H11A H 0.5202 0.4857 0.3886 0.030 Uiso 1 1 calc R . . C12 C 0.66410(13) 0.41437(11) 0.39686(9) 0.0204(3) Uani 1 1 d . . . C13 C 0.76770(13) 0.41807(11) 0.42406(9) 0.0205(3) Uani 1 1 d . . . H13A H 0.8162 0.3652 0.4143 0.025 Uiso 1 1 calc R . . C14 C 0.79976(13) 0.50013(11) 0.46578(9) 0.0195(3) Uani 1 1 d . . . H14A H 0.8710 0.5039 0.4852 0.023 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0196(2) 0.0282(2) 0.0281(2) 0.00313(16) 0.00662(16) -0.00370(16) Cl2 0.0279(2) 0.02288(19) 0.0323(2) -0.00833(16) 0.00047(18) -0.00497(17) N1 0.0265(8) 0.0190(6) 0.0205(7) 0.0010(5) -0.0041(6) -0.0020(6) N3 0.0312(9) 0.0243(7) 0.0245(7) -0.0012(6) -0.0008(6) -0.0050(6) O1 0.0180(6) 0.0349(6) 0.0271(6) 0.0031(5) -0.0017(5) 0.0062(5) O2 0.0246(6) 0.0209(5) 0.0316(6) -0.0008(5) -0.0030(5) 0.0060(5) O3 0.0357(8) 0.0373(7) 0.0517(9) -0.0114(6) -0.0154(7) -0.0045(6) O4 0.0436(8) 0.0263(6) 0.0445(8) -0.0127(6) -0.0032(7) 0.0041(6) C1 0.0362(11) 0.0211(8) 0.0420(10) 0.0046(7) -0.0064(9) 0.0033(8) C2 0.0352(10) 0.0256(8) 0.0190(8) 0.0019(7) 0.0004(7) -0.0109(8) C3 0.0266(9) 0.0310(8) 0.0224(8) -0.0017(7) 0.0054(7) -0.0057(8) C4 0.0220(9) 0.0231(7) 0.0218(8) 0.0003(6) 0.0021(7) 0.0000(7) C5 0.0230(9) 0.0179(7) 0.0183(7) -0.0004(6) -0.0023(7) -0.0016(7) C6 0.0194(8) 0.0197(7) 0.0170(7) -0.0036(6) -0.0045(6) -0.0014(7) C7 0.0168(8) 0.0181(7) 0.0219(8) -0.0017(6) 0.0034(6) -0.0013(6) C8 0.0169(8) 0.0173(7) 0.0185(7) 0.0029(6) 0.0017(6) -0.0007(6) C9 0.0164(8) 0.0179(7) 0.0180(7) 0.0020(6) 0.0002(6) -0.0005(6) C10 0.0205(8) 0.0217(7) 0.0297(9) -0.0012(7) -0.0009(7) 0.0037(7) C11 0.0182(8) 0.0282(8) 0.0277(8) -0.0011(7) -0.0042(7) -0.0018(7) C12 0.0247(9) 0.0197(7) 0.0169(7) 0.0004(6) 0.0006(6) -0.0033(7) C13 0.0219(8) 0.0197(7) 0.0199(7) 0.0016(6) 0.0009(6) 0.0037(7) C14 0.0170(8) 0.0222(7) 0.0195(7) 0.0018(6) 0.0000(6) 0.0017(7) _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 C7 1.7678(16) . ? Cl2 C7 1.7760(15) . ? N1 C1 1.460(2) . ? N1 C2 1.346(2) . ? N1 C5 1.3911(19) . ? N3 O3 1.218(2) . ? N3 O4 1.2214(19) . ? N3 C12 1.471(2) . ? O1 C6 1.2155(19) . ? O2 C8 1.1989(18) . ? C1 H1A 0.980 . ? C1 H1B 0.980 . ? C1 H1C 0.980 . ? C2 H2A 0.950 . ? C2 C3 1.372(2) . ? C3 H3A 0.950 . ? C3 C4 1.385(2) . ? C4 H4A 0.950 . ? C4 C5 1.390(2) . ? C5 C6 1.432(2) . ? C6 C7 1.566(2) . ? C7 C8 1.554(2) . ? C8 C9 1.500(2) . ? C9 C10 1.399(2) . ? C9 C14 1.388(2) . ? C10 H10A 0.950 . ? C10 C11 1.379(2) . ? C11 H11A 0.950 . ? C11 C12 1.382(2) . ? C12 C13 1.374(2) . ? C13 H13A 0.950 . ? C13 C14 1.379(2) . ? C14 H14A 0.950 . ? 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 C1 N1 C2 123.88(14) . . ? C1 N1 C5 127.82(14) . . ? C2 N1 C5 108.11(14) . . ? O3 N3 O4 123.80(14) . . ? O3 N3 C12 118.44(14) . . ? O4 N3 C12 117.75(14) . . ? N1 C1 H1A 109.5 . . ? N1 C1 H1B 109.5 . . ? N1 C1 H1C 109.5 . . ? H1A C1 H1B 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 H2A 125.1 . . ? N1 C2 C3 109.88(14) . . ? H2A C2 C3 125.1 . . ? C2 C3 H3A 126.5 . . ? C2 C3 C4 107.00(15) . . ? H3A C3 C4 126.5 . . ? C3 C4 H4A 126.0 . . ? C3 C4 C5 108.01(14) . . ? H4A C4 C5 126.0 . . ? N1 C5 C4 106.99(14) . . ? N1 C5 C6 122.56(14) . . ? C4 C5 C6 130.45(14) . . ? O1 C6 C5 125.59(14) . . ? O1 C6 C7 118.92(14) . . ? C5 C6 C7 115.49(13) . . ? Cl1 C7 Cl2 108.17(8) . . ? Cl1 C7 C6 110.15(11) . . ? Cl1 C7 C8 106.66(10) . . ? Cl2 C7 C6 107.24(10) . . ? Cl2 C7 C8 109.98(10) . . ? C6 C7 C8 114.51(12) . . ? O2 C8 C7 119.75(13) . . ? O2 C8 C9 122.03(14) . . ? C7 C8 C9 118.22(12) . . ? C8 C9 C10 116.30(13) . . ? C8 C9 C14 123.99(14) . . ? C10 C9 C14 119.70(14) . . ? C9 C10 H10A 119.8 . . ? C9 C10 C11 120.35(15) . . ? H10A C10 C11 119.8 . . ? C10 C11 H11A 120.9 . . ? C10 C11 C12 118.18(15) . . ? H11A C11 C12 120.9 . . ? N3 C12 C11 119.15(15) . . ? N3 C12 C13 118.05(14) . . ? C11 C12 C13 122.80(14) . . ? C12 C13 H13A 120.7 . . ? C12 C13 C14 118.59(15) . . ? H13A C13 C14 120.7 . . ? C9 C14 C13 120.36(15) . . ? C9 C14 H14A 119.8 . . ? C13 C14 H14A 119.8 . . ? 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 C1 N1 C2 C3 -175.86(15) . . . . ? C5 N1 C2 C3 -0.54(18) . . . . ? N1 C2 C3 C4 0.56(19) . . . . ? C2 C3 C4 C5 -0.36(19) . . . . ? C3 C4 C5 N1 0.04(18) . . . . ? C3 C4 C5 C6 179.73(15) . . . . ? C1 N1 C5 C4 175.39(15) . . . . ? C1 N1 C5 C6 -4.3(2) . . . . ? C2 N1 C5 C4 0.30(17) . . . . ? C2 N1 C5 C6 -179.42(14) . . . . ? N1 C5 C6 O1 -7.4(2) . . . . ? N1 C5 C6 C7 171.70(13) . . . . ? C4 C5 C6 O1 172.94(16) . . . . ? C4 C5 C6 C7 -8.0(2) . . . . ? O1 C6 C7 Cl1 10.26(17) . . . . ? O1 C6 C7 Cl2 -107.23(14) . . . . ? O1 C6 C7 C8 130.45(15) . . . . ? C5 C6 C7 Cl1 -168.91(11) . . . . ? C5 C6 C7 Cl2 73.60(14) . . . . ? C5 C6 C7 C8 -48.72(17) . . . . ? Cl1 C7 C8 O2 -109.14(14) . . . . ? Cl1 C7 C8 C9 71.79(14) . . . . ? Cl2 C7 C8 O2 7.92(18) . . . . ? Cl2 C7 C8 C9 -171.14(11) . . . . ? C6 C7 C8 O2 128.75(15) . . . . ? C6 C7 C8 C9 -50.32(18) . . . . ? O2 C8 C9 C10 -7.9(2) . . . . ? O2 C8 C9 C14 173.43(15) . . . . ? C7 C8 C9 C10 171.11(13) . . . . ? C7 C8 C9 C14 -7.5(2) . . . . ? C8 C9 C10 C11 -177.70(15) . . . . ? C14 C9 C10 C11 1.0(2) . . . . ? C9 C10 C11 C12 -0.3(2) . . . . ? C10 C11 C12 N3 179.94(14) . . . . ? C10 C11 C12 C13 -0.7(2) . . . . ? O3 N3 C12 C11 0.8(2) . . . . ? O3 N3 C12 C13 -178.67(15) . . . . ? O4 N3 C12 C11 -178.00(15) . . . . ? O4 N3 C12 C13 2.6(2) . . . . ? N3 C12 C13 C14 -179.64(13) . . . . ? C11 C12 C13 C14 0.9(2) . . . . ? C12 C13 C14 C9 -0.2(2) . . . . ? C8 C9 C14 C13 177.89(14) . . . . ? C10 C9 C14 C13 -0.7(2) . . . . ? _diffrn_measured_fraction_theta_max 0.873 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.342 _refine_diff_density_min -0.268 _refine_diff_density_rms 0.051 # Contents of RES file _computing_special_details ; TITL mjh77 in Pbca CELL 0.71073 12.4615 13.4977 17.2015 90.000 90.000 90.000 ZERR 8.00 0.0006 0.0005 0.0007 0.000 0.000 0.000 LATT 1 SYMM 0.5-X, -Y, 0.5+Z SYMM -X, 0.5+Y, 0.5-Z SYMM 0.5+X, 0.5-Y, -Z SFAC C H N O CL UNIT 112 80 16 32 16 TEMP -123 L.S. 8 BOND $H CONF REM colourless block SIZE 0.30 0.30 0.10 FMAP 2 PLAN 5 ACTA 50 WGHT 0.025800 1.744100 EXTI 0.001142 FVAR 0.12643 CL1 5 0.965303 0.683760 0.499291 11.00000 0.01961 0.02815 = 0.02812 0.00313 0.00662 -0.00370 CL2 5 0.868973 0.774420 0.633110 11.00000 0.02786 0.02288 = 0.03227 -0.00833 0.00047 -0.00497 N1 3 0.803058 0.457788 0.713172 11.00000 0.02646 0.01899 = 0.02050 0.00101 -0.00411 -0.00204 N3 3 0.630744 0.326189 0.352864 11.00000 0.03116 0.02432 = 0.02450 -0.00121 -0.00082 -0.00497 O1 4 0.972914 0.534492 0.615180 11.00000 0.01799 0.03488 = 0.02709 0.00309 -0.00173 0.00621 O2 4 0.694944 0.736492 0.531441 11.00000 0.02462 0.02093 = 0.03157 -0.00075 -0.00304 0.00598 O3 4 0.539655 0.323159 0.327331 11.00000 0.03572 0.03731 = 0.05173 -0.01142 -0.01542 -0.00452 O4 4 0.695916 0.259298 0.345250 11.00000 0.04365 0.02625 = 0.04454 -0.01270 -0.00319 0.00412 C1 1 0.884061 0.379732 0.710178 11.00000 0.03617 0.02107 = 0.04196 0.00461 -0.00638 0.00325 AFIX 137 H1A 2 0.861832 0.324462 0.743428 11.00000 -1.50000 H1B 2 0.952873 0.405915 0.728580 11.00000 -1.50000 H1C 2 0.891849 0.356427 0.656517 11.00000 -1.50000 AFIX 0 C2 1 0.711086 0.450937 0.753858 11.00000 0.03523 0.02561 = 0.01900 0.00189 0.00037 -0.01090 AFIX 43 H2A 2 0.692100 0.397211 0.786777 11.00000 -1.20000 AFIX 0 C3 1 0.648857 0.533075 0.740713 11.00000 0.02663 0.03102 = 0.02238 -0.00168 0.00539 -0.00572 AFIX 43 H3A 2 0.580528 0.546496 0.762824 11.00000 -1.20000 AFIX 0 C4 1 0.704549 0.592746 0.689079 11.00000 0.02197 0.02315 = 0.02182 0.00028 0.00211 0.00000 AFIX 43 H4A 2 0.680916 0.654633 0.669111 11.00000 -1.20000 AFIX 0 C5 1 0.801059 0.546186 0.671615 11.00000 0.02303 0.01790 = 0.01834 -0.00041 -0.00229 -0.00159 C6 1 0.886850 0.576111 0.621463 11.00000 0.01944 0.01974 = 0.01703 -0.00358 -0.00455 -0.00136 C7 1 0.864113 0.669899 0.570491 11.00000 0.01682 0.01809 = 0.02187 -0.00172 0.00337 -0.00126 C8 1 0.755249 0.667580 0.526408 11.00000 0.01686 0.01731 = 0.01853 0.00292 0.00168 -0.00071 C9 1 0.728508 0.577247 0.479499 11.00000 0.01635 0.01791 = 0.01796 0.00198 0.00018 -0.00046 C10 1 0.624049 0.571976 0.450055 11.00000 0.02048 0.02167 = 0.02973 -0.00120 -0.00086 0.00368 AFIX 43 H10A 2 0.575534 0.625143 0.458678 11.00000 -1.20000 AFIX 0 C11 1 0.591110 0.490032 0.408581 11.00000 0.01821 0.02825 = 0.02772 -0.00106 -0.00423 -0.00177 AFIX 43 H11A 2 0.520193 0.485681 0.388605 11.00000 -1.20000 AFIX 0 C12 1 0.664103 0.414374 0.396861 11.00000 0.02473 0.01970 = 0.01690 0.00041 0.00059 -0.00328 C13 1 0.767698 0.418068 0.424062 11.00000 0.02188 0.01966 = 0.01985 0.00163 0.00094 0.00369 AFIX 43 H13A 2 0.816207 0.365207 0.414334 11.00000 -1.20000 AFIX 0 C14 1 0.799756 0.500127 0.465778 11.00000 0.01699 0.02215 = 0.01949 0.00180 -0.00003 0.00174 AFIX 43 H14A 2 0.870984 0.503914 0.485236 11.00000 -1.20000 HKLF 4 REM mjh77 in Pbca REM R1 = 0.0323 for 2709 Fo > 4sig(Fo) and 0.0426 for all 3223 data REM 201 parameters refined using 0 restraints END ; #===END