# Electronic Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Jennifer Swift' _publ_contact_author_email JAS2@GEORGETOWN.EDU _publ_section_title ; Halogen/Methyl Exchange in a Series of Isostructural 1,3-bis(m-Dihalophenyl)Ureas ; loop_ _publ_author_name 'Jennifer Swift' 'Joseph A. Basile' 'Christina Capacci-Daniel' 'Shoaleh Dehghan' 'Rupa Hiremath' ; A.Sarjeant ; 'Victoria M. Wurster' # Attachment 'mBrMePU_done.cif' data_mBrMePU _database_code_depnum_ccdc_archive 'CCDC 695365' _audit_creation_method SHELXL-97 _chemical_name_systematic '1-(m-bromophenyl)-3-(m-tolyl) urea' _chemical_name_common mBrMePU _chemical_melting_point 247.5 _chemical_formula_moiety 'C28 H23 Br2 N4 O2' _chemical_formula_sum 'C28 H23 Br2 N4 O2' _chemical_formula_weight 607.32 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x+1/2, y+1/2, -z' 'x+1/2, -y+1/2, -z' _cell_length_a 14.612(6) _cell_length_b 9.5770(16) _cell_length_c 4.5572(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 637.7(3) _cell_formula_units_Z 1 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.581 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 305 _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_number ? _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% ? _diffrn_reflns_number 5296 _diffrn_reflns_av_R_equivalents 0.0525 _diffrn_reflns_av_sigmaI/netI 0.0430 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_limit_l_max 5 _diffrn_reflns_theta_min 4.26 _diffrn_reflns_theta_max 27.60 _diffrn_reflns_resolution_max 0.77 _reflns_number_total 1476 _reflns_number_gt 1343 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Oxford Diffraction CrysAlis CCD' _computing_cell_refinement 'Oxford Diffraction CrysAlis RED' _computing_data_reduction 'Oxford Diffraction CrysAlis RED' _computing_structure_solution 'Sheldrick, G.M. (2000). SHELXTL v6.10.' _computing_structure_refinement 'Sheldrick, G.M. (2000). SHELXTL v6.10.' _computing_molecular_graphics 'Sheldrick, G.M. (2000). SHELXTL v6.10.' _computing_publication_material 'Sheldrick, G.M. (2000). SHELXTL v6.10.' _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^)+(0.0000P)^2^+2.1441P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.06(3) _refine_ls_number_reflns 1476 _refine_ls_number_parameters 96 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0600 _refine_ls_R_factor_gt 0.0543 _refine_ls_wR_factor_ref 0.1228 _refine_ls_wR_factor_gt 0.1210 _refine_ls_goodness_of_fit_ref 1.220 _refine_ls_restrained_S_all 1.225 _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 Br1 Br 0.07989(10) 0.64891(14) 0.0545(3) 0.0306(3) Uani 0.50 1 d PD A 1 C8 C 0.1020(12) 0.645(4) 0.096(9) 0.21(3) Uani 0.50 1 d PD A 2 H8A H 0.0931 0.5448 0.1317 0.320 Uiso 0.25 1 calc PR A 2 H8B H 0.0936 0.6648 -0.1127 0.320 Uiso 0.25 1 calc PR A 2 H8C H 0.0572 0.6981 0.2110 0.320 Uiso 0.25 1 calc PR A 2 O1 O 0.5000 0.5000 0.4798(10) 0.0219(11) Uani 1 2 d S . . N1 N 0.4312(2) 0.5578(4) 0.0523(10) 0.0182(8) Uani 1 1 d . . . H1N H 0.436(4) 0.525(7) -0.150(17) 0.06(2) Uiso 1 1 d . . . C1 C 0.5000 0.5000 0.2079(15) 0.0181(14) Uani 1 2 d S . . C2 C 0.3594(3) 0.6346(5) 0.1719(9) 0.0162(9) Uani 1 1 d . . . C3 C 0.2704(3) 0.6090(5) 0.0732(12) 0.0204(9) Uani 1 1 d . A . H3 H 0.2595 0.5394 -0.0712 0.024 Uiso 1 1 calc R . . C4 C 0.1976(3) 0.6862(5) 0.1880(11) 0.0256(11) Uani 1 1 d D . . C5 C 0.2116(3) 0.7886(5) 0.3964(12) 0.0273(12) Uani 1 1 d . A . H5 H 0.1617 0.8406 0.4730 0.033 Uiso 1 1 calc R . . C6 C 0.3013(3) 0.8139(5) 0.4924(11) 0.0279(12) Uani 1 1 d . . . H6 H 0.3122 0.8840 0.6359 0.033 Uiso 1 1 calc R A . C7 C 0.3745(3) 0.7379(5) 0.3804(10) 0.0229(11) Uani 1 1 d . A . H7 H 0.4349 0.7567 0.4465 0.027 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 Br1 0.0152(4) 0.0366(5) 0.0401(6) 0.0045(6) 0.0012(5) 0.0036(4) C8 0.09(2) 0.33(6) 0.22(4) -0.19(4) -0.04(2) -0.02(2) O1 0.022(2) 0.035(3) 0.009(3) 0.000 0.000 0.0071(19) N1 0.0130(17) 0.0277(19) 0.0137(16) -0.0013(17) -0.0049(17) 0.0035(15) C1 0.014(3) 0.022(3) 0.018(4) 0.000 0.000 -0.002(2) C2 0.0170(18) 0.020(2) 0.011(2) 0.0024(19) 0.0006(15) 0.0012(18) C3 0.018(2) 0.024(2) 0.019(2) 0.002(2) 0.0012(18) 0.0019(16) C4 0.022(2) 0.028(3) 0.026(3) 0.009(2) 0.008(2) 0.0019(19) C5 0.027(2) 0.028(2) 0.027(3) 0.006(2) 0.012(2) 0.012(2) C6 0.033(2) 0.028(3) 0.023(3) -0.003(2) 0.004(2) 0.007(2) C7 0.020(2) 0.031(3) 0.018(3) 0.001(2) 0.0012(17) 0.0016(19) _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 C4 1.859(5) . ? C8 C4 1.511(11) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? O1 C1 1.239(8) . ? N1 C1 1.349(5) . ? N1 C2 1.392(5) . ? N1 H1N 0.97(7) . ? C1 N1 1.349(5) 2_665 ? C2 C7 1.389(6) . ? C2 C3 1.398(6) . ? C3 C4 1.397(6) . ? C3 H3 0.9500 . ? C4 C5 1.380(7) . ? C5 C6 1.402(7) . ? C5 H5 0.9500 . ? C6 C7 1.391(6) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 C8 H8A 109.5 . . ? C4 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C4 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C1 N1 C2 124.9(4) . . ? C1 N1 H1N 108(4) . . ? C2 N1 H1N 126(4) . . ? O1 C1 N1 121.7(3) . 2_665 ? O1 C1 N1 121.7(3) . . ? N1 C1 N1 116.5(6) 2_665 . ? C7 C2 N1 121.7(4) . . ? C7 C2 C3 119.5(4) . . ? N1 C2 C3 118.8(4) . . ? C4 C3 C2 119.7(4) . . ? C4 C3 H3 120.2 . . ? C2 C3 H3 120.2 . . ? C5 C4 C3 121.4(4) . . ? C5 C4 C8 120.9(14) . . ? C3 C4 C8 117.5(14) . . ? C5 C4 Br1 119.9(4) . . ? C3 C4 Br1 118.7(4) . . ? C4 C5 C6 118.5(4) . . ? C4 C5 H5 120.8 . . ? C6 C5 H5 120.8 . . ? C7 C6 C5 120.8(5) . . ? C7 C6 H6 119.6 . . ? C5 C6 H6 119.6 . . ? C2 C7 C6 120.2(4) . . ? C2 C7 H7 119.9 . . ? C6 C7 H7 119.9 . . ? 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 C2 N1 C1 O1 7.0(5) . . . . ? C2 N1 C1 N1 -173.0(5) . . . 2_665 ? C1 N1 C2 C7 45.9(6) . . . . ? C1 N1 C2 C3 -135.8(4) . . . . ? C7 C2 C3 C4 -0.9(7) . . . . ? N1 C2 C3 C4 -179.2(4) . . . . ? C2 C3 C4 C5 0.5(7) . . . . ? C2 C3 C4 C8 -174(2) . . . . ? C2 C3 C4 Br1 -179.5(4) . . . . ? C3 C4 C5 C6 -0.1(7) . . . . ? C8 C4 C5 C6 174(2) . . . . ? Br1 C4 C5 C6 179.9(4) . . . . ? C4 C5 C6 C7 0.0(8) . . . . ? N1 C2 C7 C6 179.1(5) . . . . ? C3 C2 C7 C6 0.8(7) . . . . ? C5 C6 C7 C2 -0.4(8) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.60 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.353 _refine_diff_density_min -0.527 _refine_diff_density_rms 0.086 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 2' _symmetry_int_tables_number 18 _symmetry_space_group_name_Hall 'P 2 2ab' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist -11.00 11.00 0.00 0.0281 -10.00 -12.00 0.00 0.0127 13.00 -10.00 0.00 0.0279 2.00 3.00 6.00 0.2403 19.00 5.00 0.00 0.0329 7.00 13.00 0.00 0.0269 2.00 1.00 -6.00 0.2424 -20.00 3.00 0.00 0.0326 _audit_creation_date ; 'Wed Nov 01 11:40:40 2006' ; _audit_creation_method_reference ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.30.5 (release 12-06-2006 CrysAlis171 .NET) (compiled Jun 12 2006,17:01:16) ; _computing_data_collection_reference ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.30.5 (release 12-06-2006 CrysAlis171 .NET) (compiled Jun 12 2006,17:01:16) ; _computing_cell_refinment_reference ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.30.5 (release 12-06-2006 CrysAlis171 .NET) (compiled Jun 12 2006,17:01:16) ; _computing_data_reduction_reference ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.30.5 (release 12-06-2006 CrysAlis171 .NET) (compiled Jun 12 2006,17:01:16) ; _cell_measurement_temperature 110 _cell_measurement_reflns_used 3368 _cell_measurement_theta_min 4.1699 _cell_measurement_theta_max 27.4991 _cell_measurement_resolution_max 0.77 _exptl_crystal_size_max 0.2424 _exptl_crystal_size_mid 0.0805 _exptl_crystal_size_min 0.0127 _exptl_absorpt_coefficient_mu 3.212 _exptl_absorpt_correction_T_min 0.475 _exptl_absorpt_correction_T_max 0.888 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.30.5 (release 12-06-2006 CrysAlis171 .NET) (compiled Jun 12 2006,17:01:16) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 15.9890 _diffrn_orient_matrix_UB_11 -0.0408943476 _diffrn_orient_matrix_UB_12 -0.0697893338 _diffrn_orient_matrix_UB_13 0.0097873498 _diffrn_orient_matrix_UB_21 -0.0024384520 _diffrn_orient_matrix_UB_22 0.0158965117 _diffrn_orient_matrix_UB_23 0.0473556473 _diffrn_orient_matrix_UB_31 -0.1499387900 _diffrn_orient_matrix_UB_32 0.0187449249 _diffrn_orient_matrix_UB_33 -0.0034363117 _diffrn_measurement_details 'see scan set' _diffrn_measurement_method ' omega phi scans' _diffrn_source_power 2 _diffrn_source_voltage 50 _diffrn_source_current 40 _diffrn_measurement_device Kappa _diffrn_measurement_device_type Xcalibur3 _diffrn_ambient_temperature 110 _exptl_crystal_recrystallization_method benzene #===END # Attachment 'mBrPU_done.cif' data_mbrpu _database_code_depnum_ccdc_archive 'CCDC 695366' _audit_creation_method SHELXL-97 _chemical_name_systematic '1,3-bis(m-bromophenyl) urea' _chemical_name_common mBrPU _chemical_melting_point 273.9 _chemical_formula_moiety 'C13 H10 Br2 N2 O' _chemical_formula_sum 'C13 H10 Br2 N2 O' _chemical_formula_weight 370.05 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x+1/2, y+1/2, -z' 'x+1/2, -y+1/2, -z' _cell_length_a 9.5460(11) _cell_length_b 14.7549(15) _cell_length_c 4.5585(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 642.07(14) _cell_formula_units_Z 2 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.914 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 360 _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_number ? _diffrn_standards_interval_count 1 _diffrn_standards_interval_time 50 _diffrn_standards_decay_% ? _diffrn_reflns_number 8169 _diffrn_reflns_av_R_equivalents 0.0498 _diffrn_reflns_av_sigmaI/netI 0.0322 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 4.27 _diffrn_reflns_theta_max 29.08 _diffrn_reflns_resolution_max 0.73 _reflns_number_total 1717 _reflns_number_gt 1661 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Oxford Diffraction CrysAlis CCD' _computing_cell_refinement 'Oxford Diffraction CrysAlis RED' _computing_data_reduction 'Oxford Diffraction CrysAlis RED' _computing_structure_solution 'Sheldrick, G.M. (2000). SHELXTL v6.10.' _computing_structure_refinement 'Sheldrick, G.M. (2000). SHELXTL v6.10.' _computing_molecular_graphics 'Sheldrick, G.M. (2000). SHELXTL v6.10.' _computing_publication_material 'Sheldrick, G.M. (2000). SHELXTL v6.10.' _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^)+(0.0167P)^2^+1.6883P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.022(17) _refine_ls_number_reflns 1717 _refine_ls_number_parameters 83 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0380 _refine_ls_R_factor_gt 0.0362 _refine_ls_wR_factor_ref 0.0686 _refine_ls_wR_factor_gt 0.0676 _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 Br1 Br 0.84972(4) 0.08145(2) 0.44065(9) 0.02795(11) Uani 1 1 d . . . O1 O 1.0000 0.5000 0.0189(7) 0.0208(8) Uani 1 2 d S . . N1 N 0.9435(3) 0.43085(17) 0.4511(6) 0.0136(5) Uani 1 1 d . . . H1A H 0.9574 0.4304 0.6419 0.016 Uiso 1 1 calc R . . C1 C 1.0000 0.5000 0.2917(10) 0.0142(9) Uani 1 2 d S . . C2 C 0.8641(4) 0.36001(19) 0.3264(6) 0.0130(6) Uani 1 1 d . . . C3 C 0.8896(3) 0.2717(2) 0.4257(8) 0.0152(6) Uani 1 1 d . . . H3A H 0.9592 0.2604 0.5700 0.018 Uiso 1 1 calc R . . C4 C 0.8115(4) 0.2010(2) 0.3101(8) 0.0188(7) Uani 1 1 d . . . C5 C 0.7081(4) 0.2147(2) 0.0983(8) 0.0191(7) Uani 1 1 d . . . H5A H 0.6559 0.1655 0.0205 0.023 Uiso 1 1 calc R . . C6 C 0.6845(4) 0.3035(2) 0.0053(7) 0.0213(8) Uani 1 1 d . . . H6A H 0.6146 0.3149 -0.1382 0.026 Uiso 1 1 calc R . . C7 C 0.7610(4) 0.3755(2) 0.1182(7) 0.0180(7) Uani 1 1 d . . . H7A H 0.7428 0.4355 0.0526 0.022 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 Br1 0.03216(19) 0.01307(15) 0.03861(19) 0.00066(15) 0.00128(19) -0.00268(16) O1 0.0292(19) 0.0234(18) 0.0097(18) 0.000 0.000 -0.0098(15) N1 0.0180(12) 0.0114(12) 0.0114(10) -0.0029(12) 0.0011(11) -0.0038(10) C1 0.018(2) 0.012(2) 0.012(2) 0.000 0.000 -0.0009(18) C2 0.0175(15) 0.0114(13) 0.0100(12) -0.0018(10) 0.0020(13) -0.0024(13) C3 0.0161(14) 0.0151(14) 0.0144(13) -0.0014(13) 0.0032(13) -0.0006(11) C4 0.0229(17) 0.0140(15) 0.0193(16) -0.0010(13) 0.0025(13) 0.0000(13) C5 0.0181(16) 0.0204(16) 0.0188(17) -0.0023(13) 0.0028(13) -0.0055(13) C6 0.0218(18) 0.0251(17) 0.0171(19) -0.0029(12) -0.0019(12) -0.0036(14) C7 0.0210(17) 0.0180(16) 0.0152(17) -0.0011(12) 0.0010(13) -0.0021(14) _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 C4 1.897(3) . ? O1 C1 1.243(6) . ? N1 C1 1.364(3) . ? N1 C2 1.411(4) . ? N1 H1A 0.8800 . ? C1 N1 1.364(3) 2_765 ? C2 C7 1.386(5) . ? C2 C3 1.401(4) . ? C3 C4 1.385(5) . ? C3 H3A 0.9500 . ? C4 C5 1.395(5) . ? C5 C6 1.395(5) . ? C5 H5A 0.9500 . ? C6 C7 1.388(5) . ? C6 H6A 0.9500 . ? C7 H7A 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C2 123.5(3) . . ? C1 N1 H1A 118.2 . . ? C2 N1 H1A 118.2 . . ? O1 C1 N1 122.2(2) . . ? O1 C1 N1 122.2(2) . 2_765 ? N1 C1 N1 115.6(4) . 2_765 ? C7 C2 C3 119.9(3) . . ? C7 C2 N1 122.3(3) . . ? C3 C2 N1 117.8(3) . . ? C4 C3 C2 118.9(3) . . ? C4 C3 H3A 120.5 . . ? C2 C3 H3A 120.5 . . ? C3 C4 C5 122.3(3) . . ? C3 C4 Br1 118.5(3) . . ? C5 C4 Br1 119.2(3) . . ? C6 C5 C4 117.4(3) . . ? C6 C5 H5A 121.3 . . ? C4 C5 H5A 121.3 . . ? C7 C6 C5 121.4(3) . . ? C7 C6 H6A 119.3 . . ? C5 C6 H6A 119.3 . . ? C2 C7 C6 120.1(3) . . ? C2 C7 H7A 120.0 . . ? C6 C7 H7A 120.0 . . ? 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 C2 N1 C1 O1 -8.9(3) . . . . ? C2 N1 C1 N1 171.1(3) . . . 2_765 ? C1 N1 C2 C7 -44.4(4) . . . . ? C1 N1 C2 C3 137.3(3) . . . . ? C7 C2 C3 C4 0.7(5) . . . . ? N1 C2 C3 C4 179.0(3) . . . . ? C2 C3 C4 C5 -0.1(5) . . . . ? C2 C3 C4 Br1 178.7(2) . . . . ? C3 C4 C5 C6 -0.3(5) . . . . ? Br1 C4 C5 C6 -179.2(3) . . . . ? C4 C5 C6 C7 0.2(5) . . . . ? C3 C2 C7 C6 -0.9(5) . . . . ? N1 C2 C7 C6 -179.1(3) . . . . ? C5 C6 C7 C2 0.4(5) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 29.08 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.654 _refine_diff_density_min -0.833 _refine_diff_density_rms 0.105 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 2' _symmetry_int_tables_number 18 _symmetry_space_group_name_Hall 'P 2 2ab' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist -10.00 -14.00 1.00 0.0486 10.00 -15.00 0.00 0.0185 1.00 1.00 -6.00 0.3200 -1.00 -1.00 6.00 0.2956 -9.00 13.00 3.00 0.1366 3.00 -20.00 0.00 0.0123 -11.00 -12.00 0.00 0.0155 11.00 12.00 0.00 0.0124 -9.00 16.00 0.00 0.0185 _audit_creation_date ; 'Thu Jul 14 13:23:07 2005' ; _audit_creation_method_reference ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET) (compiled Apr 1 2005,17:53:34) ; _computing_data_collection_reference ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET) (compiled Apr 1 2005,17:53:34) ; _computing_cell_refinment_reference ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET) (compiled Apr 1 2005,17:53:34) ; _computing_data_reduction_reference ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET) (compiled Apr 1 2005,17:53:34) ; _cell_measurement_theta_min 4.1351 _cell_measurement_theta_max 28.9932 _cell_measurement_resolution_max 0.73 _cell_measurement_temperature 110 _exptl_crystal_size_max 0.32000 _exptl_crystal_size_mid 0.09754 _exptl_crystal_size_min 0.01231 _exptl_absorpt_coefficient_mu 6.30072 _exptl_absorpt_correction_T_min 0.23571 _exptl_absorpt_correction_T_max 0.85632 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET) (compiled Apr 1 2005,17:53:34) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. ; _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 15.9890 _diffrn_orient_matrix_UB_11 -0.0112271755 _diffrn_orient_matrix_UB_12 -0.0639829484 _diffrn_orient_matrix_UB_13 -0.0241408655 _diffrn_orient_matrix_UB_21 0.0036623704 _diffrn_orient_matrix_UB_22 -0.0375952840 _diffrn_orient_matrix_UB_23 0.0414844495 _diffrn_orient_matrix_UB_31 -0.1551491134 _diffrn_orient_matrix_UB_32 0.0037196847 _diffrn_orient_matrix_UB_33 0.0026839577 _diffrn_measurement_details 'see scan set' _diffrn_measurement_method ' omega scans' _diffrn_source_power 2 _diffrn_source_voltage 50 _diffrn_source_current 40 _diffrn_measurement_device Kappa _diffrn_measurement_device_type Xcalibur3 _diffrn_ambient_temperature 110 _exptl_crystal_recrystallization_method benzene #===END # Attachment 'mClMePU_done.cif' data_mClMePU _database_code_depnum_ccdc_archive 'CCDC 695367' _audit_creation_method SHELXL-97 _chemical_name_systematic '1-(m-chlorophenyl)-3-(m-tolyl) urea' _chemical_name_common '1-(m-chlorophenyl)-3-(m-tolyl) urea' _chemical_melting_point 235.3 _chemical_formula_moiety 'C14 H13 Cl N2 O' _chemical_formula_sum 'C14 H13 Cl N2 O' _chemical_formula_weight 260.71 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x+1/2, y+1/2, -z' 'x+1/2, -y+1/2, -z' _cell_length_a 9.5777(5) _cell_length_b 14.3646(7) _cell_length_c 4.5596(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 627.31(5) _cell_formula_units_Z 2 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.380 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 272 _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_number ? _diffrn_standards_interval_count 1 _diffrn_standards_interval_time 50 _diffrn_standards_decay_% ? _diffrn_reflns_number 9349 _diffrn_reflns_av_R_equivalents 0.0459 _diffrn_reflns_av_sigmaI/netI 0.0298 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 4.47 _diffrn_reflns_theta_max 28.55 _diffrn_reflns_resolution_max 0.74 _reflns_number_total 1597 _reflns_number_gt 1387 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Oxford Diffraction CrysAlis CCD' _computing_cell_refinement 'Oxford Diffraction CrysAlis RED' _computing_data_reduction 'Oxford Diffraction CrysAlis RED' _computing_structure_solution 'Sheldrick, G.M. (2000). SHELXTL v6.10.' _computing_structure_refinement 'Sheldrick, G.M. (2000). SHELXTL v6.10.' _computing_molecular_graphics 'Sheldrick, G.M. (2000). SHELXTL v6.10.' _computing_publication_material 'Sheldrick, G.M. (2000). SHELXTL v6.10.' _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. Chloro-methyl disorder at C4 resulted in oscillating parameters which prevented refinement to convergence. Two restraints where used to fix the position of these atoms and eliminate oscillation. ; _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^)+(0.0595P)^2^+0.0000P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.06(11) _refine_ls_number_reflns 1597 _refine_ls_number_parameters 97 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0492 _refine_ls_R_factor_gt 0.0410 _refine_ls_wR_factor_ref 0.1026 _refine_ls_wR_factor_gt 0.0983 _refine_ls_goodness_of_fit_ref 1.118 _refine_ls_restrained_S_all 1.122 _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 0.6550(3) 0.58164(15) 0.9402(8) 0.0412(5) Uani 0.50 1 d PD A 1 N1 N 0.55787(13) 0.93033(9) 0.9576(3) 0.0218(3) Uani 1 1 d . . . H1 H 0.551(2) 0.9356(16) 1.136(5) 0.040(6) Uiso 1 1 d . . . O1 O 0.5000 1.0000 0.5266(3) 0.0260(4) Uani 1 2 d S . . C1 C 0.5000 1.0000 0.7981(5) 0.0208(5) Uani 1 2 d S . . C2 C 0.63557(16) 0.85650(10) 0.8323(3) 0.0216(3) Uani 1 1 d . . . C3 C 0.60927(16) 0.76637(11) 0.9306(4) 0.0245(3) Uani 1 1 d . A . H3 H 0.5397 0.7553 1.0750 0.029 Uiso 1 1 calc R . . C4 C 0.68584(18) 0.69281(10) 0.8154(4) 0.0290(4) Uani 1 1 d D . . C5 C 0.78656(18) 0.70853(12) 0.6062(4) 0.0332(4) Uani 1 1 d . A . H5 H 0.8381 0.6580 0.5267 0.040 Uiso 1 1 calc R . . C6 C 0.81241(19) 0.79855(13) 0.5124(4) 0.0340(4) Uani 1 1 d . . . H6 H 0.8822 0.8094 0.3683 0.041 Uiso 1 1 calc R A . C7 C 0.73825(16) 0.87289(12) 0.6253(4) 0.0273(4) Uani 1 1 d . A . H7 H 0.7576 0.9345 0.5616 0.033 Uiso 1 1 calc R . . C8 C 0.6491(17) 0.5944(5) 0.903(4) 0.069(5) Uani 0.50 1 d PD A 2 H8A H 0.5839 0.5681 0.7592 0.104 Uiso 0.50 1 calc PR A 2 H8B H 0.6055 0.5947 1.0970 0.104 Uiso 0.50 1 calc PR A 2 H8C H 0.7342 0.5565 0.9082 0.104 Uiso 0.50 1 calc PR A 2 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 0.0448(8) 0.0179(4) 0.0609(11) -0.0002(6) -0.0079(7) 0.0026(5) N1 0.0294(7) 0.0197(6) 0.0162(6) -0.0014(5) 0.0022(5) 0.0034(5) O1 0.0340(9) 0.0255(8) 0.0184(8) 0.000 0.000 0.0064(6) C1 0.0226(10) 0.0203(10) 0.0196(10) 0.000 0.000 -0.0021(8) C2 0.0240(7) 0.0209(7) 0.0200(7) -0.0031(6) -0.0036(6) 0.0025(6) C3 0.0238(7) 0.0224(7) 0.0272(8) -0.0004(7) -0.0039(7) 0.0015(6) C4 0.0310(8) 0.0204(7) 0.0357(9) -0.0049(7) -0.0099(7) 0.0042(6) C5 0.0323(9) 0.0343(9) 0.0328(9) -0.0109(7) -0.0069(8) 0.0134(7) C6 0.0289(8) 0.0450(10) 0.0280(9) -0.0040(8) 0.0011(7) 0.0077(8) C7 0.0265(8) 0.0284(8) 0.0269(9) -0.0008(7) -0.0005(7) 0.0019(6) C8 0.084(7) 0.055(7) 0.069(7) 0.000(4) 0.010(5) 0.024(4) _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 C4 1.721(3) . ? N1 C1 1.3555(17) . ? N1 C2 1.4159(19) . ? N1 H1 0.82(2) . ? O1 C1 1.238(3) . ? C1 N1 1.3554(17) 2_675 ? C2 C7 1.383(2) . ? C2 C3 1.393(2) . ? C3 C4 1.390(2) . ? C3 H3 0.9500 . ? C4 C5 1.375(2) . ? C4 C8 1.510(5) . ? C5 C6 1.384(3) . ? C5 H5 0.9500 . ? C6 C7 1.382(2) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C2 123.47(14) . . ? C1 N1 H1 115.5(16) . . ? C2 N1 H1 120.8(16) . . ? O1 C1 N1 122.43(9) . 2_675 ? O1 C1 N1 122.43(9) . . ? N1 C1 N1 115.14(19) 2_675 . ? C7 C2 C3 120.43(15) . . ? C7 C2 N1 121.43(14) . . ? C3 C2 N1 118.10(14) . . ? C4 C3 C2 119.31(15) . . ? C4 C3 H3 120.3 . . ? C2 C3 H3 120.3 . . ? C5 C4 C3 120.51(15) . . ? C5 C4 C8 120.0(7) . . ? C3 C4 C8 119.3(7) . . ? C5 C4 Cl1 120.15(17) . . ? C3 C4 Cl1 119.34(18) . . ? C4 C5 C6 119.54(15) . . ? C4 C5 H5 120.2 . . ? C6 C5 H5 120.2 . . ? C7 C6 C5 120.99(17) . . ? C7 C6 H6 119.5 . . ? C5 C6 H6 119.5 . . ? C6 C7 C2 119.21(16) . . ? C6 C7 H7 120.4 . . ? C2 C7 H7 120.4 . . ? C4 C8 H8A 109.5 . . ? C4 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C4 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? 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 C2 N1 C1 O1 6.67(15) . . . . ? C2 N1 C1 N1 -173.33(15) . . . 2_675 ? C1 N1 C2 C7 46.7(2) . . . . ? C1 N1 C2 C3 -135.53(14) . . . . ? C7 C2 C3 C4 -1.0(2) . . . . ? N1 C2 C3 C4 -178.80(15) . . . . ? C2 C3 C4 C5 0.0(2) . . . . ? C2 C3 C4 C8 -174.8(7) . . . . ? C2 C3 C4 Cl1 179.18(17) . . . . ? C3 C4 C5 C6 0.6(2) . . . . ? C8 C4 C5 C6 175.4(7) . . . . ? Cl1 C4 C5 C6 -178.61(18) . . . . ? C4 C5 C6 C7 -0.2(3) . . . . ? C5 C6 C7 C2 -0.8(3) . . . . ? C3 C2 C7 C6 1.4(2) . . . . ? N1 C2 C7 C6 179.16(15) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 28.55 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.191 _refine_diff_density_min -0.200 _refine_diff_density_rms 0.045 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 2' _symmetry_int_tables_number 18 _symmetry_space_group_name_Hall 'P 2 2ab' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 12.00 10.00 0.00 0.0452 -12.00 -9.00 0.00 0.0248 7.00 -7.00 -5.00 0.1924 11.00 -11.00 0.00 0.0436 -11.00 11.00 0.00 0.0218 9.00 -6.00 5.00 0.1762 _audit_creation_date ; 'Fri Jun 30 15:37:57 2006' ; _audit_creation_method_reference ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.5 (release 22-02-2006 CrysAlis171 .NET) (compiled Feb 22 2006,13:01:44) ; _computing_data_collection_reference ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.29.5 (release 22-02-2006 CrysAlis171 .NET) (compiled Feb 22 2006,13:01:44) ; _computing_cell_refinment_reference ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.5 (release 22-02-2006 CrysAlis171 .NET) (compiled Feb 22 2006,13:01:44) ; _computing_data_reduction_reference ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.5 (release 22-02-2006 CrysAlis171 .NET) (compiled Feb 22 2006,13:01:44) ; _cell_measurement_reflns_used ? _cell_measurement_theta_min 4.2476 _cell_measurement_theta_max 28.4915 _cell_measurement_resolution_max 0.74 _cell_measurement_temperature 110 _exptl_crystal_size_max 0.1923 _exptl_crystal_size_mid 0.0840 _exptl_crystal_size_min 0.0218 _exptl_absorpt_coefficient_mu 0.293 _exptl_absorpt_correction_T_min 0.892 _exptl_absorpt_correction_T_max 0.985 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.29.5 (release 22-02-2006 CrysAlis171 .NET) (compiled Feb 22 2006,13:01:44) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 15.9890 _diffrn_orient_matrix_UB_11 -0.0189040031 _diffrn_orient_matrix_UB_12 0.0463916780 _diffrn_orient_matrix_UB_13 0.0380088770 _diffrn_orient_matrix_UB_21 -0.1056461910 _diffrn_orient_matrix_UB_22 0.0380503592 _diffrn_orient_matrix_UB_23 -0.0259155703 _diffrn_orient_matrix_UB_31 -0.1126077590 _diffrn_orient_matrix_UB_32 -0.0434104360 _diffrn_orient_matrix_UB_33 0.0179422285 _diffrn_measurement_details 'see scan set' loop_ _diffrn_scan_number _diffrn_scan_type _diffrn_scan_start _diffrn_scan_end _diffrn_scan_width _diffrn_scan_exptime _diffrn_scan_omega _diffrn_scan_theta _diffrn_scan_kappa _diffrn_scan_phi _diffrn_scan_omega1 _diffrn_scan_theta1 _diffrn_scan_frames 1 omega 48.00 95.00 1.00 35.00 - 24.85 58.00 -29.00 0.00 0.00 47 2 omega 48.00 95.00 1.00 35.00 - 24.85 58.00 170.00 0.00 0.00 47 3 omega 5.00 57.00 1.00 35.00 - 24.85 -75.00 240.00 0.00 0.00 52 4 omega 1.00 48.00 1.00 35.00 - 24.85 58.00 170.00 0.00 0.00 47 5 omega -19.00 30.00 1.00 35.00 - -25.62 95.00 89.00 0.00 0.00 49 6 omega -49.00 -2.00 1.00 35.00 - -25.62 58.00 -29.00 0.00 0.00 47 7 omega -40.00 4.00 1.00 35.00 - -25.62 124.00 22.00 0.00 0.00 44 8 omega -19.00 25.00 1.00 35.00 - -25.62 95.00 -90.00 0.00 0.00 44 9 omega -48.00 2.00 1.00 35.00 - -25.62 -45.00 240.00 0.00 0.00 50 10 omega -68.00 -19.00 1.00 35.00 - -25.62 95.00 -159.00 0.00 0.00 49 11 omega -98.00 -48.00 1.00 35.00 - -25.62 -45.00 240.00 0.00 0.00 50 12 omega -68.00 -19.00 1.00 35.00 - -25.62 95.00 89.00 0.00 0.00 49 13 omega -68.00 -30.00 1.00 35.00 - -25.62 95.00 20.00 0.00 0.00 38 14 omega -2.00 45.00 1.00 35.00 - -25.62 58.00 170.00 0.00 0.00 47 15 omega -31.00 -3.00 1.00 35.00 - -25.62 45.00 240.00 0.00 0.00 28 16 omega -49.00 -21.00 1.00 35.00 - -25.62 58.00 170.00 0.00 0.00 28 17 omega -3.00 25.00 1.00 35.00 - -25.62 45.00 240.00 0.00 0.00 28 _diffrn_measurement_method ' omega scans' _diffrn_source_power 2 _diffrn_source_voltage 50 _diffrn_source_current 40 _diffrn_measurement_device Kappa _diffrn_measurement_device_type Xcalibur3 _diffrn_ambient_temperature 110 _exptl_crystal_recrystallization_method benzene #===END #===END # Attachment 'mClPU_done.CIF' data_mClPU _database_code_depnum_ccdc_archive 'CCDC 695368' _audit_creation_method SHELXL-97 _chemical_name_systematic 1,3-bis(m-chlorophenyl)urea _chemical_name_common mClPU _chemical_melting_point 244.7 _chemical_formula_moiety 'C13 H10 Cl2 N2 O' _chemical_formula_sum 'C13 H10 Cl2 N2 O' _chemical_formula_weight 281.13 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' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/2, -y+1/2, -z' '-x+1/2, y+1/2, -z' _cell_length_a 9.5880(8) _cell_length_b 14.3214(11) _cell_length_c 4.5653(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 626.88(9) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4966 _cell_measurement_theta_min 2.557 _cell_measurement_theta_max 28.320 _exptl_crystal_description needles _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.489 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 288 _exptl_absorpt_coefficient_mu 0.505 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8430 _exptl_absorpt_correction_T_max 0.9512 _exptl_absorpt_process_details 'SADABS, G. Sheldrick (1999)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'SMART platform CCD, Siemens' _diffrn_measurement_method 'omega scans' _diffrn_reflns_number 5490 _diffrn_reflns_av_R_equivalents 0.0238 _diffrn_reflns_av_sigmaI/netI 0.0175 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 5 _diffrn_reflns_theta_min 2.56 _diffrn_reflns_theta_max 27.98 _reflns_number_total 1483 _reflns_number_gt 1425 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART, Siemens' _computing_cell_refinement 'SAINT, Siemens' _computing_data_reduction 'SAINT, Siemens' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-SEED, L.Barbour(1999); http://x-seed.net/' _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^)+(0.0398P)^2^+0.1283P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.007(7) _refine_ls_number_reflns 1483 _refine_ls_number_parameters 87 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0277 _refine_ls_R_factor_gt 0.0263 _refine_ls_wR_factor_ref 0.0715 _refine_ls_wR_factor_gt 0.0707 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.15472(5) 0.41943(3) 0.42691(12) 0.04928(15) Uani 1 1 d . . . N1 N 0.05747(12) 0.06999(8) 0.4604(2) 0.0221(2) Uani 1 1 d . . . O1 O 0.0000 0.0000 0.0298(3) 0.0271(3) Uani 1 2 d S . . C3 C 0.11132(13) 0.23404(9) 0.4291(3) 0.0245(3) Uani 1 1 d . . . H3 H 0.0418 0.2464 0.5721 0.029 Uiso 1 1 calc R . . C2 C 0.13663(13) 0.14327(8) 0.3352(3) 0.0210(2) Uani 1 1 d . . . C5 C 0.29065(15) 0.29061(11) 0.1015(3) 0.0337(3) Uani 1 1 d . . . H5 H 0.3423 0.3410 0.0209 0.040 Uiso 1 1 calc R . . C1 C 0.0000 0.0000 0.3013(4) 0.0197(3) Uani 1 2 d S . . C7 C 0.23972(14) 0.12572(10) 0.1277(3) 0.0268(3) Uani 1 1 d . . . H7 H 0.2581 0.0636 0.0658 0.032 Uiso 1 1 calc R . . C4 C 0.18934(15) 0.30625(9) 0.3104(3) 0.0298(3) Uani 1 1 d . . . C6 C 0.31539(15) 0.19964(12) 0.0119(3) 0.0338(3) Uani 1 1 d . . . H6 H 0.3852 0.1877 -0.1309 0.041 Uiso 1 1 calc R . . H1 H 0.0478(16) 0.0671(12) 0.636(4) 0.025(4) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0573(3) 0.01981(18) 0.0708(3) 0.00019(19) -0.0043(2) -0.00693(16) N1 0.0312(5) 0.0211(5) 0.0138(5) -0.0001(4) 0.0014(4) -0.0050(4) O1 0.0374(7) 0.0295(7) 0.0144(6) 0.000 0.000 -0.0106(6) C3 0.0257(6) 0.0228(6) 0.0251(6) 0.0003(5) -0.0039(5) -0.0020(4) C2 0.0243(6) 0.0213(6) 0.0175(5) 0.0028(4) -0.0030(5) -0.0037(4) C5 0.0320(7) 0.0364(8) 0.0326(7) 0.0112(6) -0.0065(6) -0.0151(6) C1 0.0218(8) 0.0204(8) 0.0169(7) 0.000 0.000 -0.0004(6) C7 0.0266(6) 0.0304(7) 0.0235(6) -0.0005(5) 0.0007(5) -0.0033(5) C4 0.0318(7) 0.0226(6) 0.0350(7) 0.0038(6) -0.0106(6) -0.0048(5) C6 0.0274(6) 0.0458(9) 0.0280(7) 0.0038(6) 0.0033(5) -0.0092(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C4 1.7379(15) . ? N1 C1 1.3552(14) . ? N1 C2 1.4157(15) . ? N1 H1 0.807(19) . ? O1 C1 1.239(2) . ? C3 C4 1.3867(18) . ? C3 C2 1.3901(18) . ? C3 H3 0.9500 . ? C2 C7 1.3918(18) . ? C5 C4 1.379(2) . ? C5 C6 1.386(2) . ? C5 H5 0.9500 . ? C1 N1 1.3552(14) 2 ? C7 C6 1.388(2) . ? C7 H7 0.9500 . ? C6 H6 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C2 123.34(11) . . ? C1 N1 H1 116.5(12) . . ? C2 N1 H1 120.0(12) . . ? C4 C3 C2 118.87(13) . . ? C4 C3 H3 120.6 . . ? C2 C3 H3 120.6 . . ? C3 C2 C7 120.18(12) . . ? C3 C2 N1 118.36(11) . . ? C7 C2 N1 121.45(11) . . ? C4 C5 C6 118.50(13) . . ? C4 C5 H5 120.7 . . ? C6 C5 H5 120.7 . . ? O1 C1 N1 122.43(8) . . ? O1 C1 N1 122.43(8) . 2 ? N1 C1 N1 115.14(15) . 2 ? C6 C7 C2 119.51(13) . . ? C6 C7 H7 120.2 . . ? C2 C7 H7 120.2 . . ? C5 C4 C3 121.93(13) . . ? C5 C4 Cl1 119.84(11) . . ? C3 C4 Cl1 118.22(12) . . ? C5 C6 C7 121.01(14) . . ? C5 C6 H6 119.5 . . ? C7 C6 H6 119.5 . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.98 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.258 _refine_diff_density_min -0.204 _refine_diff_density_rms 0.040 _exptl_crystal_recrystallization_method ethanol _symmetry_cell_setting orthorhombic _symmetry_space_group_name_h-m 'P 21 21 2' _symmetry_int_tables_number 18 _symmetry_space_group_name_Hall 'P 2 2ab' #===END # Attachment 'mIPU_done.cif' data_mIPU _database_code_depnum_ccdc_archive 'CCDC 695369' _audit_creation_method SHELXL-97 _chemical_name_systematic '1,3-bis(m-iodophenyl) urea' _chemical_name_common mIPU _chemical_melting_point 282.8 _chemical_formula_moiety 'C13 H10 I2 N2 O' _chemical_formula_sum 'C13 H10 I2 N2 O' _chemical_formula_weight 464.03 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x+1/2, y+1/2, -z' 'x+1/2, -y+1/2, -z' _cell_length_a 9.6345(11) _cell_length_b 15.3998(14) _cell_length_c 4.5673(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 677.65(15) _cell_formula_units_Z 2 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.274 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 432 _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_number ? _diffrn_standards_interval_count 1 _diffrn_standards_interval_time 50 _diffrn_standards_decay_% ? _diffrn_reflns_number 6763 _diffrn_reflns_av_R_equivalents 0.0326 _diffrn_reflns_av_sigmaI/netI 0.0225 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 5 _diffrn_reflns_theta_min 4.43 _diffrn_reflns_theta_max 28.06 _diffrn_reflns_resolution_max 0.76 _reflns_number_total 1641 _reflns_number_gt 1605 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Oxford Diffraction CrysAlis CCD' _computing_cell_refinement 'Oxford Diffraction CrysAlis RED' _computing_data_reduction 'Oxford Diffraction CrysAlis RED' _computing_structure_solution 'Sheldrick, G.M. (2000). SHELXTL v6.10.' _computing_structure_refinement 'Sheldrick, G.M. (2000). SHELXTL v6.10.' _computing_molecular_graphics 'Sheldrick, G.M. (2000). SHELXTL v6.10.' _computing_publication_material 'Sheldrick, G.M. (2000). SHELXTL v6.10.' _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^)+(0.0150P)^2^+0.8840P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.04(3) _refine_ls_number_reflns 1641 _refine_ls_number_parameters 83 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0210 _refine_ls_R_factor_gt 0.0201 _refine_ls_wR_factor_ref 0.0417 _refine_ls_wR_factor_gt 0.0413 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.073 _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 I1 I 0.85282(2) 0.086243(12) 0.03574(5) 0.02056(7) Uani 1 1 d . . . O1 O 1.0000 0.5000 0.5031(8) 0.0205(7) Uani 1 2 d S . . N1 N 0.9452(3) 0.43330(14) 0.0689(6) 0.0120(5) Uani 1 1 d . . . H1N H 0.9594 0.4334 -0.1214 0.014 Uiso 1 1 calc R . . C1 C 1.0000 0.5000 0.2315(10) 0.0121(8) Uani 1 2 d S . . C2 C 0.8670(3) 0.36438(19) 0.1911(6) 0.0120(6) Uani 1 1 d . . . C3 C 0.8912(3) 0.28076(19) 0.0844(7) 0.0129(6) Uani 1 1 d . . . H3A H 0.9608 0.2709 -0.0593 0.016 Uiso 1 1 calc R . . C4 C 0.8122(3) 0.2122(2) 0.1912(7) 0.0141(6) Uani 1 1 d . . . C5 C 0.7092(3) 0.2251(2) 0.4002(7) 0.0161(6) Uani 1 1 d . . . H5A H 0.6554 0.1779 0.4712 0.019 Uiso 1 1 calc R . . C6 C 0.6870(3) 0.3091(2) 0.5024(8) 0.0163(6) Uani 1 1 d . . . H6A H 0.6174 0.3190 0.6459 0.020 Uiso 1 1 calc R . . C7 C 0.7645(3) 0.3787(2) 0.3993(7) 0.0143(6) Uani 1 1 d . . . H7A H 0.7475 0.4356 0.4706 0.017 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 I1 0.02301(10) 0.00986(8) 0.02883(11) -0.00176(8) -0.00047(9) -0.00195(9) O1 0.0296(17) 0.0227(15) 0.0093(17) 0.000 0.000 -0.0111(13) N1 0.0126(11) 0.0102(11) 0.0131(11) 0.0013(10) 0.0012(11) -0.0019(9) C1 0.015(2) 0.0093(19) 0.012(2) 0.000 0.000 0.0007(16) C2 0.0122(15) 0.0138(13) 0.0101(13) 0.0014(10) -0.0032(13) -0.0009(12) C3 0.0131(14) 0.0150(13) 0.0107(14) 0.0010(11) -0.0002(11) 0.0001(10) C4 0.0163(16) 0.0106(14) 0.0155(15) 0.0020(12) -0.0035(12) 0.0000(11) C5 0.0133(14) 0.0183(14) 0.0168(16) 0.0031(12) -0.0004(12) -0.0035(12) C6 0.0148(14) 0.0223(14) 0.0117(16) -0.0004(13) 0.0004(12) -0.0010(11) C7 0.0161(15) 0.0137(13) 0.0131(15) -0.0015(11) -0.0013(12) 0.0023(12) _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 I1 C4 2.102(3) . ? O1 C1 1.240(6) . ? N1 C1 1.373(3) . ? N1 C2 1.416(4) . ? N1 H1N 0.8800 . ? C1 N1 1.373(3) 2_765 ? C2 C7 1.389(4) . ? C2 C3 1.397(4) . ? C3 C4 1.390(4) . ? C3 H3A 0.9500 . ? C4 C5 1.392(4) . ? C5 C6 1.391(4) . ? C5 H5A 0.9500 . ? C6 C7 1.388(4) . ? C6 H6A 0.9500 . ? C7 H7A 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C2 123.5(3) . . ? C1 N1 H1N 118.2 . . ? C2 N1 H1N 118.2 . . ? O1 C1 N1 122.74(19) . 2_765 ? O1 C1 N1 122.74(19) . . ? N1 C1 N1 114.5(4) 2_765 . ? C7 C2 C3 120.3(3) . . ? C7 C2 N1 122.0(3) . . ? C3 C2 N1 117.7(3) . . ? C4 C3 C2 119.1(3) . . ? C4 C3 H3A 120.4 . . ? C2 C3 H3A 120.4 . . ? C3 C4 C5 121.5(3) . . ? C3 C4 I1 118.7(2) . . ? C5 C4 I1 119.8(2) . . ? C6 C5 C4 118.2(3) . . ? C6 C5 H5A 120.9 . . ? C4 C5 H5A 120.9 . . ? C7 C6 C5 121.4(3) . . ? C7 C6 H6A 119.3 . . ? C5 C6 H6A 119.3 . . ? C6 C7 C2 119.5(3) . . ? C6 C7 H7A 120.3 . . ? C2 C7 H7A 120.3 . . ? 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 C2 N1 C1 O1 9.0(3) . . . . ? C2 N1 C1 N1 -171.0(3) . . . 2_765 ? C1 N1 C2 C7 44.1(4) . . . . ? C1 N1 C2 C3 -139.0(2) . . . . ? C7 C2 C3 C4 -0.5(4) . . . . ? N1 C2 C3 C4 -177.4(3) . . . . ? C2 C3 C4 C5 0.4(5) . . . . ? C2 C3 C4 I1 -178.6(2) . . . . ? C3 C4 C5 C6 -0.3(5) . . . . ? I1 C4 C5 C6 178.7(2) . . . . ? C4 C5 C6 C7 0.3(5) . . . . ? C5 C6 C7 C2 -0.4(5) . . . . ? C3 C2 C7 C6 0.5(5) . . . . ? N1 C2 C7 C6 177.3(3) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 28.06 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.750 _refine_diff_density_min -0.895 _refine_diff_density_rms 0.099 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 2' _symmetry_int_tables_number 18 _symmetry_space_group_name_Hall 'P 2 2ab' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0.00 -1.00 6.00 0.2585 13.00 4.00 0.00 0.0185 13.00 -7.00 0.00 0.0169 -13.00 -4.00 0.00 0.0154 0.00 -22.00 0.00 0.0277 0.00 22.00 0.00 0.0108 2.00 4.00 -6.00 0.2535 -13.00 7.00 0.00 0.0092 _audit_creation_date ; 'Wed Jul 13 15:02:00 2005' ; _audit_creation_method_reference ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET) (compiled Apr 1 2005,17:53:34) ; _computing_data_collection_reference ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET) (compiled Apr 1 2005,17:53:34) ; _computing_cell_refinment_reference ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET) (compiled Apr 1 2005,17:53:34) ; _computing_data_reduction_reference ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET) (compiled Apr 1 2005,17:53:34) ; _cell_measurement_theta_min 3.9616 _cell_measurement_theta_max 27.9945 _cell_measurement_resolution_max 0.76 _cell_measurement_temperature 110 _exptl_crystal_size_max 0.25850 _exptl_crystal_size_mid 0.07631 _exptl_crystal_size_min 0.00923 _exptl_absorpt_coefficient_mu 4.63032 _exptl_absorpt_correction_T_min 0.49796 _exptl_absorpt_correction_T_max 0.89283 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET) (compiled Apr 1 2005,17:53:34) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. ; _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 15.9890 _diffrn_orient_matrix_UB_11 0.0063037809 _diffrn_orient_matrix_UB_12 -0.0667429280 _diffrn_orient_matrix_UB_13 0.0193207806 _diffrn_orient_matrix_UB_21 -0.0063538643 _diffrn_orient_matrix_UB_22 -0.0310473965 _diffrn_orient_matrix_UB_23 -0.0417361795 _diffrn_orient_matrix_UB_31 0.1550416368 _diffrn_orient_matrix_UB_32 0.0012334506 _diffrn_orient_matrix_UB_33 -0.0024948420 _diffrn_measurement_details 'see scan set' _diffrn_measurement_method ' omega scans' _diffrn_source_power 2 _diffrn_source_voltage 50 _diffrn_source_current 40 _diffrn_measurement_device Kappa _diffrn_measurement_device_type Xcalibur3 _diffrn_ambient_temperature 110 _exptl_crystal_recrystallization_method benzene #===END # Attachment 'mMePU_done.cif' data_mMePU _database_code_depnum_ccdc_archive 'CCDC 695370' _audit_creation_method SHELXL-97 _chemical_name_systematic '1,3-bis(tolyl) urea' _chemical_name_common mMePU _chemical_melting_point 222.6 _chemical_formula_moiety 'C15 H16 N2 O' _chemical_formula_sum 'C15 H16 N2 O' _chemical_formula_weight 240.30 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' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x+1/2, y+1/2, -z' 'x+1/2, -y+1/2, -z' _cell_length_a 9.5950(16) _cell_length_b 14.521(2) _cell_length_c 4.5902(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 639.6(2) _cell_formula_units_Z 2 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.248 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 256 _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_number ? _diffrn_standards_interval_count 1 _diffrn_standards_interval_time 50 _diffrn_standards_decay_% ? _diffrn_reflns_number 717 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0275 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 5 _diffrn_reflns_theta_min 4.25 _diffrn_reflns_theta_max 25.31 _diffrn_reflns_resolution_max 0.83 _reflns_number_total 717 _reflns_number_gt 705 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Oxford Diffraction CrysAlis CCD' _computing_cell_refinement 'Oxford Diffraction CrysAlis RED' _computing_data_reduction 'Oxford Diffraction CrysAlis RED' _computing_structure_solution 'Sheldrick, G.M. (2000). SHELXTL v6.10.' _computing_structure_refinement 'Sheldrick, G.M. (2000). SHELXTL v6.10.' _computing_molecular_graphics 'Sheldrick, G.M. (2000). SHELXTL v6.10.' _computing_publication_material 'Sheldrick, G.M. (2000). SHELXTL v6.10.' _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^)+(0.0388P)^2^+0.3931P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -7(5) _refine_ls_number_reflns 717 _refine_ls_number_parameters 88 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0596 _refine_ls_R_factor_gt 0.0580 _refine_ls_wR_factor_ref 0.1140 _refine_ls_wR_factor_gt 0.1132 _refine_ls_goodness_of_fit_ref 1.213 _refine_ls_restrained_S_all 1.213 _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 N1 N 0.5592(3) 0.06846(17) 0.4535(7) 0.0200(6) Uani 1 1 d . . . H1N H 0.546(4) 0.065(2) 0.643(9) 0.032(10) Uiso 1 1 d . . . O1 O 0.5000 0.0000 0.0233(7) 0.0252(8) Uani 1 2 d S . . C1 C 0.5000 0.0000 0.2940(10) 0.0177(10) Uani 1 2 d S . . C2 C 0.6352(3) 0.1432(2) 0.3319(7) 0.0193(7) Uani 1 1 d . . . C3 C 0.6079(3) 0.2314(2) 0.4325(8) 0.0241(8) Uani 1 1 d . . . H3A H 0.5385 0.2406 0.5771 0.029 Uiso 1 1 calc R . . C4 C 0.6815(3) 0.3066(2) 0.3230(8) 0.0279(8) Uani 1 1 d . . . C5 C 0.7834(4) 0.2914(2) 0.1138(8) 0.0325(9) Uani 1 1 d . . . H5A H 0.8350 0.3419 0.0385 0.039 Uiso 1 1 calc R . . C6 C 0.8105(4) 0.2033(2) 0.0139(8) 0.0328(9) Uani 1 1 d . . . H6A H 0.8799 0.1939 -0.1306 0.039 Uiso 1 1 calc R . . C7 C 0.7372(3) 0.1288(2) 0.1228(7) 0.0256(8) Uani 1 1 d . . . H7A H 0.7567 0.0683 0.0550 0.031 Uiso 1 1 calc R . . C8 C 0.6493(4) 0.4025(2) 0.4335(11) 0.0447(12) Uani 1 1 d . . . H8A H 0.7294 0.4428 0.3979 0.067 Uiso 1 1 calc R . . H8B H 0.6301 0.4000 0.6431 0.067 Uiso 1 1 calc R . . H8C H 0.5675 0.4267 0.3312 0.067 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 N1 0.0288(15) 0.0174(13) 0.0137(14) -0.0021(11) 0.0008(13) -0.0061(11) O1 0.0318(18) 0.0288(17) 0.0151(17) 0.000 0.000 -0.0050(14) C1 0.020(2) 0.014(2) 0.019(2) 0.000 0.000 0.0035(18) C2 0.0172(15) 0.0213(15) 0.0192(16) 0.0021(14) -0.0033(15) -0.0028(13) C3 0.0211(17) 0.0237(16) 0.0275(19) 0.0023(14) -0.0038(16) -0.0018(13) C4 0.0258(17) 0.0227(17) 0.035(2) 0.0089(17) -0.0133(17) -0.0046(14) C5 0.0284(19) 0.036(2) 0.033(2) 0.0128(17) -0.0096(17) -0.0157(16) C6 0.0250(17) 0.048(2) 0.0250(19) 0.0056(19) 0.0015(16) -0.0105(16) C7 0.0249(18) 0.0288(18) 0.0233(19) 0.0003(14) -0.0010(15) -0.0019(14) C8 0.048(2) 0.0215(17) 0.065(3) 0.0010(19) -0.010(3) -0.0056(16) _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 N1 C1 1.359(3) . ? N1 C2 1.422(4) . ? N1 H1N 0.88(4) . ? O1 C1 1.243(6) . ? C1 N1 1.359(3) 2_655 ? C2 C3 1.386(4) . ? C2 C7 1.387(4) . ? C3 C4 1.394(4) . ? C3 H3A 0.9500 . ? C4 C5 1.388(5) . ? C4 C8 1.514(5) . ? C5 C6 1.383(5) . ? C5 H5A 0.9500 . ? C6 C7 1.384(5) . ? C6 H6A 0.9500 . ? C7 H7A 0.9500 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C2 124.2(3) . . ? C1 N1 H1N 115(2) . . ? C2 N1 H1N 120(2) . . ? O1 C1 N1 122.58(19) . 2_655 ? O1 C1 N1 122.58(19) . . ? N1 C1 N1 114.8(4) 2_655 . ? C3 C2 C7 120.2(3) . . ? C3 C2 N1 118.5(3) . . ? C7 C2 N1 121.2(3) . . ? C2 C3 C4 120.5(3) . . ? C2 C3 H3A 119.7 . . ? C4 C3 H3A 119.7 . . ? C5 C4 C3 118.8(3) . . ? C5 C4 C8 121.5(3) . . ? C3 C4 C8 119.7(3) . . ? C6 C5 C4 120.6(3) . . ? C6 C5 H5A 119.7 . . ? C4 C5 H5A 119.7 . . ? C5 C6 C7 120.5(3) . . ? C5 C6 H6A 119.7 . . ? C7 C6 H6A 119.7 . . ? C6 C7 C2 119.4(3) . . ? C6 C7 H7A 120.3 . . ? C2 C7 H7A 120.3 . . ? C4 C8 H8A 109.5 . . ? C4 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C4 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? 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 C2 N1 C1 O1 -4.6(3) . . . . ? C2 N1 C1 N1 175.4(3) . . . 2_655 ? C1 N1 C2 C3 134.3(3) . . . . ? C1 N1 C2 C7 -47.4(4) . . . . ? C7 C2 C3 C4 0.6(5) . . . . ? N1 C2 C3 C4 178.9(3) . . . . ? C2 C3 C4 C5 -0.6(5) . . . . ? C2 C3 C4 C8 179.4(3) . . . . ? C3 C4 C5 C6 0.6(5) . . . . ? C8 C4 C5 C6 -179.5(3) . . . . ? C4 C5 C6 C7 -0.6(5) . . . . ? C5 C6 C7 C2 0.6(5) . . . . ? C3 C2 C7 C6 -0.6(5) . . . . ? N1 C2 C7 C6 -178.9(3) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.31 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.141 _refine_diff_density_min -0.172 _refine_diff_density_rms 0.043 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 2' _symmetry_int_tables_number 18 _symmetry_space_group_name_Hall 'P 2 2ab' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist -4.00 20.00 0.00 0.0233 4.00 -20.00 0.00 0.0139 12.00 10.00 0.00 0.0186 -13.00 -2.00 0.00 0.0083 4.00 3.00 6.00 0.3101 -5.00 -3.00 -6.00 0.3099 _audit_creation_date ; 'Thu Nov 03 12:20:53 2005' ; _audit_creation_method_reference ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET) (compiled Apr 1 2005,17:53:34) ; _computing_data_collection_reference ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET) (compiled Apr 1 2005,17:53:34) ; _computing_cell_refinment_reference ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET) (compiled Apr 1 2005,17:53:34) ; _computing_data_reduction_reference ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET) (compiled Apr 1 2005,17:53:34) ; _cell_measurement_theta_min 2.52 _cell_measurement_theta_max 26.80 _cell_measurement_resolution_max 0.79 _cell_measurement_reflns_used 1851 _cell_measurement_temperature 110 _exptl_crystal_size_max 0.31008 _exptl_crystal_size_mid 0.11401 _exptl_crystal_size_min 0.00829 _exptl_absorpt_coefficient_mu 0.07971 _exptl_absorpt_correction_T_min 0.97524 _exptl_absorpt_correction_T_max 0.99799 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET) (compiled Apr 1 2005,17:53:34) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. ; _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 15.9890 _diffrn_orient_matrix_UB_11 -0.0666423348 _diffrn_orient_matrix_UB_12 0.0576674779 _diffrn_orient_matrix_UB_13 0.0221322736 _diffrn_orient_matrix_UB_21 0.0078096259 _diffrn_orient_matrix_UB_22 0.0386036239 _diffrn_orient_matrix_UB_23 -0.0415773333 _diffrn_orient_matrix_UB_31 -0.1391980509 _diffrn_orient_matrix_UB_32 -0.0254749263 _diffrn_orient_matrix_UB_33 -0.0129443282 _diffrn_measurement_details 'see scan set' _diffrn_measurement_method ' omega scans' _diffrn_source_power 2 _diffrn_source_voltage 50 _diffrn_source_current 40 _diffrn_measurement_device Kappa _diffrn_measurement_device_type Xcalibur3 _diffrn_ambient_temperature 110 _exptl_crystal_recrystallization_method '1:1 (v/v) ethanol:acetonitrile' #===END # Attachment 'mBrMePU_done.CIF' data_mBrMePU _database_code_depnum_ccdc_archive 'CCDC 700260' _audit_creation_method SHELXL-97 _chemical_name_systematic '1-(m-bromophenyl)-3-(m-tolyl) urea' _chemical_name_common mBrMePU _chemical_melting_point 247.5 _chemical_formula_moiety 'C14 H13 Br N2 O' _chemical_formula_sum 'C14 H13 Br N2 O' _chemical_formula_weight 305.17 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/2, -y+1/2, -z' '-x+1/2, y+1/2, -z' _cell_length_a 9.5770(16) _cell_length_b 14.612(6) _cell_length_c 4.5572(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 637.7(3) _cell_formula_units_Z 2 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.589 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 308 _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_standards_number ? _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% ? _diffrn_reflns_number 5296 _diffrn_reflns_av_R_equivalents 0.0525 _diffrn_reflns_av_sigmaI/netI 0.0430 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_limit_l_max 5 _diffrn_reflns_theta_min 4.26 _diffrn_reflns_theta_max 27.60 _reflns_number_total 1476 _reflns_number_gt 1343 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Oxford Diffraction CrysAlis CCD' _computing_cell_refinement 'Oxford Diffraction CrysAlis RED' _computing_data_reduction 'Oxford Diffraction CrysAlis RED' _computing_structure_solution 'Sheldrick, G.M. (2000). SHELXTL v6.10.' _computing_structure_refinement 'Sheldrick, G.M. (2000). SHELXTL v6.10.' _computing_molecular_graphics 'Sheldrick, G.M. (2000). SHELXTL v6.10.' _computing_publication_material 'Sheldrick, G.M. (2000). SHELXTL v6.10.' _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. Bromo-methyl disorder at C4 resulted in oscillating parameters which prevented refinement to convergence. Two restraints where used to fix the position of these atoms and eliminate oscillation. ; _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^)+(0.0000P)^2^+2.1196P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.06(3) _refine_ls_number_reflns 1476 _refine_ls_number_parameters 79 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0599 _refine_ls_R_factor_gt 0.0543 _refine_ls_wR_factor_ref 0.1222 _refine_ls_wR_factor_gt 0.1205 _refine_ls_goodness_of_fit_ref 1.217 _refine_ls_restrained_S_all 1.221 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.4423(4) 0.0688(2) 0.4477(9) 0.0180(7) Uani 1 1 d . . . O1 O 0.5000 0.0000 0.0202(10) 0.0216(10) Uani 1 2 d S . . C2 C 0.3654(5) 0.1406(3) 0.3279(9) 0.0162(9) Uani 1 1 d . . . C3 C 0.3910(5) 0.2296(3) 0.4268(12) 0.0202(9) Uani 1 1 d . A . H3 H 0.4605 0.2406 0.5714 0.024 Uiso 1 1 calc R . . C1 C 0.5000 0.0000 0.2918(15) 0.0179(13) Uani 1 2 d S . . C4 C 0.3138(5) 0.3024(3) 0.3117(11) 0.0253(11) Uani 1 1 d D . . C5 C 0.2115(5) 0.2884(3) 0.1035(12) 0.0272(11) Uani 1 1 d . A . H5 H 0.1594 0.3383 0.0269 0.033 Uiso 1 1 calc R . . C7 C 0.2620(5) 0.1255(3) 0.1195(10) 0.0226(10) Uani 1 1 d . A . H7 H 0.2431 0.0651 0.0535 0.027 Uiso 1 1 calc R . . C6 C 0.1862(5) 0.1987(3) 0.0076(11) 0.0276(11) Uani 1 1 d . . . H6 H 0.1162 0.1879 -0.1360 0.033 Uiso 1 1 calc R A . Br1 Br 0.3510(6) 0.4201(1) 0.4454(5) 0.0303(9) Uani 0.50 1 d PD A 1 C8 C 0.3576(3) 0.3978(1) 0.4011(2) 0.202(6) Uani 0.50 1 d PD A 2 H8A H 0.3848 0.4326 0.2264 0.304 Uiso 0.50 1 calc PR A 2 H8B H 0.4370 0.3941 0.5363 0.304 Uiso 0.50 1 calc PR A 2 H8C H 0.2794 0.4286 0.4986 0.304 Uiso 0.50 1 calc PR A 2 H1 H 0.471(6) 0.062(4) 0.651(16) 0.05(2) 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 N1 0.0277(19) 0.0128(16) 0.0135(16) -0.0048(16) -0.0013(17) 0.0037(14) O1 0.035(3) 0.022(2) 0.008(3) 0.000 0.000 0.0074(19) C2 0.020(2) 0.0167(18) 0.0113(19) 0.0006(15) 0.0023(18) 0.0013(18) C3 0.024(2) 0.0173(19) 0.019(2) 0.0010(18) 0.002(2) 0.0019(16) C1 0.022(3) 0.014(3) 0.018(4) 0.000 0.000 -0.002(2) C4 0.028(3) 0.022(2) 0.026(3) 0.008(2) 0.009(2) 0.0018(19) C5 0.027(2) 0.027(2) 0.027(3) 0.012(2) 0.006(2) 0.0117(19) C7 0.030(2) 0.020(2) 0.018(2) 0.0012(17) 0.001(2) 0.0016(18) C6 0.027(2) 0.033(2) 0.022(3) 0.0040(19) -0.003(2) 0.0065(19) Br1 0.036 0.015 0.040 0.001 0.005 0.004 C8 0.299 0.090 0.219 -0.045 -0.180 -0.010 _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 N1 C1 1.349(5) . ? N1 C2 1.393(5) . ? N1 H1 0.97(7) . ? O1 C1 1.238(8) . ? C2 C7 1.389(6) . ? C2 C3 1.399(5) . ? C3 C4 1.397(6) . ? C3 H3 0.9500 . ? C1 N1 1.349(5) 2_655 ? C4 C5 1.380(7) . ? C4 C8 1.512(4) . ? C4 Br1 1.859(4) . ? C5 C6 1.402(7) . ? C5 H5 0.9500 . ? C7 C6 1.390(6) . ? C7 H7 0.9500 . ? C6 H6 0.9500 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C2 124.8(4) . . ? C1 N1 H1 108(3) . . ? C2 N1 H1 127(4) . . ? C7 C2 N1 121.7(4) . . ? C7 C2 C3 119.5(4) . . ? N1 C2 C3 118.8(4) . . ? C4 C3 C2 119.6(4) . . ? C4 C3 H3 120.2 . . ? C2 C3 H3 120.2 . . ? O1 C1 N1 121.8(3) . . ? O1 C1 N1 121.8(3) . 2_655 ? N1 C1 N1 116.5(6) . 2_655 ? C5 C4 C3 121.4(4) . . ? C5 C4 C8 121.3(4) . . ? C3 C4 C8 117.0(4) . . ? C5 C4 Br1 119.9(3) . . ? C3 C4 Br1 118.7(4) . . ? C4 C5 C6 118.4(4) . . ? C4 C5 H5 120.8 . . ? C6 C5 H5 120.8 . . ? C2 C7 C6 120.1(4) . . ? C2 C7 H7 120.0 . . ? C6 C7 H7 120.0 . . ? C7 C6 C5 121.0(5) . . ? C7 C6 H6 119.5 . . ? C5 C6 H6 119.5 . . ? C4 C8 H8A 109.5 . . ? C4 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C4 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.60 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.339 _refine_diff_density_min -0.544 _refine_diff_density_rms 0.087 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 2' _symmetry_int_tables_number 18 _symmetry_space_group_name_Hall 'P 2 2ab' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist -11.00 11.00 0.00 0.0281 -10.00 -12.00 0.00 0.0127 13.00 -10.00 0.00 0.0279 2.00 3.00 6.00 0.2403 19.00 5.00 0.00 0.0329 7.00 13.00 0.00 0.0269 2.00 1.00 -6.00 0.2424 -20.00 3.00 0.00 0.0326 _audit_creation_date ; 'Wed Nov 01 11:40:40 2006' ; _audit_creation_method_reference ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.30.5 (release 12-06-2006 CrysAlis171 .NET) (compiled Jun 12 2006,17:01:16) ; _computing_data_collection_reference ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.30.5 (release 12-06-2006 CrysAlis171 .NET) (compiled Jun 12 2006,17:01:16) ; _computing_cell_refinment_reference ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.30.5 (release 12-06-2006 CrysAlis171 .NET) (compiled Jun 12 2006,17:01:16) ; _computing_data_reduction_reference ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.30.5 (release 12-06-2006 CrysAlis171 .NET) (compiled Jun 12 2006,17:01:16) ; _cell_measurement_temperature 110 _cell_measurement_reflns_used 3368 _cell_measurement_theta_min 4.1699 _cell_measurement_theta_max 27.4991 _cell_measurement_resolution_max 0.77 _exptl_crystal_size_max 0.2424 _exptl_crystal_size_mid 0.0805 _exptl_crystal_size_min 0.0127 _exptl_absorpt_coefficient_mu 3.212 _exptl_absorpt_correction_T_min 0.475 _exptl_absorpt_correction_T_max 0.888 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.30.5 (release 12-06-2006 CrysAlis171 .NET) (compiled Jun 12 2006,17:01:16) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 15.9890 _diffrn_orient_matrix_UB_11 -0.0408943476 _diffrn_orient_matrix_UB_12 -0.0697893338 _diffrn_orient_matrix_UB_13 0.0097873498 _diffrn_orient_matrix_UB_21 -0.0024384520 _diffrn_orient_matrix_UB_22 0.0158965117 _diffrn_orient_matrix_UB_23 0.0473556473 _diffrn_orient_matrix_UB_31 -0.1499387900 _diffrn_orient_matrix_UB_32 0.0187449249 _diffrn_orient_matrix_UB_33 -0.0034363117 _diffrn_measurement_details 'see scan set' loop_ _diffrn_scan_number _diffrn_scan_type _diffrn_scan_start _diffrn_scan_end _diffrn_scan_width _diffrn_scan_exptime _diffrn_scan_omega _diffrn_scan_theta _diffrn_scan_kappa _diffrn_scan_phi _diffrn_scan_omega1 _diffrn_scan_theta1 _diffrn_scan_frames 1 omega -7.00 45.00 1.00 60.00 - 24.85 75.00 240.00 0.00 0.00 52 2 omega 28.00 74.00 1.00 60.00 - 24.85 -107.00 117.00 0.00 0.00 46 3 omega 45.00 96.00 1.00 60.00 - 24.85 75.00 240.00 0.00 0.00 51 4 omega -7.00 28.00 1.00 60.00 - 24.85 -107.00 143.00 0.00 0.00 35 5 omega -49.00 -21.00 1.00 60.00 - 24.85 147.00 102.00 0.00 0.00 28 6 omega -41.00 3.00 1.00 60.00 - -25.62 125.00 140.00 0.00 0.00 44 7 phi 0.00 180.00 1.00 60.00 0.00 -30.00 45.00 - 0.00 0.00 180 8 omega -68.00 -29.00 1.00 60.00 - -32.00 31.00 0.00 0.00 0.00 39 _diffrn_measurement_method 'omega phi scans' _diffrn_source_power 2 _diffrn_source_voltage 50 _diffrn_source_current 40 _diffrn_measurement_device Kappa _diffrn_measurement_device_type Xcalibur3 _diffrn_ambient_temperature 110 _exptl_crystal_recrystallization_method benzene