# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2014 ####################################################################### # # 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_121128_s1_zjf _audit_creation_date 2012-11-29 _audit_creation_method ; Olex2 1.1 (compiled 2011.11.01 svn.r2039, GUI svn.r3906) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C21 H18 Br N O4' _chemical_formula_sum 'C21 H18 Br N O4' _chemical_formula_weight 428.27 _chemical_absolute_configuration ad _chemical_melting_point ? _chemical_oxdiff_formula C12H14N2O3 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' Br Br -0.2901 2.4595 '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' _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_H-M_alt 'P 21 21 21' _space_group_name_Hall 'P 2ac 2ab' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, -y, z+1/2' 3 'x+1/2, -y+1/2, -z' 4 '-x, y+1/2, -z+1/2' _cell_length_a 8.1267(3) _cell_length_b 14.4806(7) _cell_length_c 15.9625(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1878.47(16) _cell_formula_units_Z 4 _cell_measurement_reflns_used 1704 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 28.8834 _cell_measurement_theta_min 2.8684 _exptl_absorpt_coefficient_mu 2.215 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.97033 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.514 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 872 _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.20 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0247 _diffrn_reflns_av_unetI/netI 0.0616 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 5787 _diffrn_reflns_theta_full 26.37 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_min 2.87 _diffrn_ambient_temperature 293.15 _diffrn_detector_area_resol_mean 16.0874 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -4.00 23.00 1.0000 7.0000 omega____ theta____ kappa____ phi______ frames - -16.8924 -99.0000 -120.0000 27 #__ type_ start__ end____ width___ exp.time_ 2 omega -43.00 53.00 1.0000 7.0000 omega____ theta____ kappa____ phi______ frames - -16.8924 37.0000 -120.0000 96 #__ type_ start__ end____ width___ exp.time_ 3 omega -29.00 6.00 1.0000 7.0000 omega____ theta____ kappa____ phi______ frames - -16.8924 19.0000 30.0000 35 ; _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0138380000 _diffrn_orient_matrix_UB_12 -0.0358561000 _diffrn_orient_matrix_UB_13 0.0294343000 _diffrn_orient_matrix_UB_21 0.0010244000 _diffrn_orient_matrix_UB_22 -0.0329186000 _diffrn_orient_matrix_UB_23 -0.0328725000 _diffrn_orient_matrix_UB_31 0.0862234000 _diffrn_orient_matrix_UB_32 -0.0053817000 _diffrn_orient_matrix_UB_33 0.0050842000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_source_current n/a _diffrn_source_voltage n/a _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 2590 _reflns_number_total 3577 _reflns_odcompleteness_completeness 99.64 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. 2008). A64, 112-122 ; _computing_structure_solution ; SHELXS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.357 _refine_diff_density_min -0.373 _refine_diff_density_rms 0.051 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.013(10) _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 246 _refine_ls_number_reflns 3577 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0775 _refine_ls_R_factor_gt 0.0476 _refine_ls_restrained_S_all 1.016 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0244P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0697 _refine_ls_wR_factor_ref 0.0789 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 -0.72699(5) -0.71231(3) 0.00581(3) 0.07025(18) Uani 1 1 d . . . O1 O -0.5155(3) -0.92082(18) 0.29573(15) 0.0407(7) Uani 1 1 d . . . O2 O -0.4824(4) -0.9001(2) 0.43059(17) 0.0714(10) Uani 1 1 d . . . O3 O -0.0258(3) -0.9919(2) 0.26867(17) 0.0564(9) Uani 1 1 d . . . O4 O -0.4635(3) -1.1250(2) 0.27612(19) 0.0584(8) Uani 1 1 d . . . N1 N -0.6051(4) -1.0879(2) 0.1558(2) 0.0413(8) Uani 1 1 d . . . C1 C -0.5062(4) -1.0703(3) 0.2235(2) 0.0393(10) Uani 1 1 d . . . C2 C -0.4615(4) -0.9657(3) 0.2196(2) 0.0332(9) Uani 1 1 d . . . C3 C -0.5676(4) -0.9313(3) 0.1492(2) 0.0329(9) Uani 1 1 d . . . C4 C -0.6475(4) -1.0063(3) 0.1129(2) 0.0379(9) Uani 1 1 d . . . C5 C -0.7527(4) -0.9954(3) 0.0458(2) 0.0476(10) Uani 1 1 d . . . H5 H -0.8062 -1.0457 0.0220 0.057 Uiso 1 1 calc R . . C6 C -0.7760(4) -0.9062(3) 0.0149(2) 0.0496(10) Uani 1 1 d . . . H6 H -0.8461 -0.8965 -0.0303 0.060 Uiso 1 1 calc R . . C7 C -0.6958(4) -0.8328(3) 0.0510(2) 0.0425(10) Uani 1 1 d . . . C8 C -0.5905(4) -0.8430(3) 0.1185(2) 0.0383(9) Uani 1 1 d . . . H8 H -0.5374 -0.7924 0.1423 0.046 Uiso 1 1 calc R . . C9 C -0.2763(4) -0.9507(2) 0.2041(2) 0.0349(8) Uani 1 1 d . . . H9 H -0.2611 -0.8851 0.1909 0.042 Uiso 1 1 calc R . . C10 C -0.1838(4) -0.9694(3) 0.2833(2) 0.0412(10) Uani 1 1 d . . . C11 C -0.2529(5) -0.9579(3) 0.3581(2) 0.0476(10) Uani 1 1 d . . . H11 H -0.1921 -0.9706 0.4060 0.057 Uiso 1 1 calc R . . C12 C -0.4185(5) -0.9262(3) 0.3662(3) 0.0480(10) Uani 1 1 d . . . C13 C -0.2161(5) -1.0054(3) 0.1286(2) 0.0542(11) Uani 1 1 d . . . H13A H -0.2222 -1.0703 0.1406 0.081 Uiso 1 1 calc R . . H13B H -0.1042 -0.9889 0.1165 0.081 Uiso 1 1 calc R . . H13C H -0.2839 -0.9916 0.0810 0.081 Uiso 1 1 calc R . . C14 C 0.0766(5) -1.0079(3) 0.3406(3) 0.0745(15) Uani 1 1 d . . . H14A H 0.1860 -1.0232 0.3226 0.112 Uiso 1 1 calc R . . H14B H 0.0323 -1.0580 0.3729 0.112 Uiso 1 1 calc R . . H14C H 0.0800 -0.9532 0.3745 0.112 Uiso 1 1 calc R . . C15 C -0.6534(5) -1.1816(3) 0.1314(2) 0.0500(11) Uani 1 1 d . . . H15A H -0.5756 -1.2250 0.1554 0.060 Uiso 1 1 calc R . . H15B H -0.6461 -1.1868 0.0710 0.060 Uiso 1 1 calc R . . C16 C -0.8252(4) -1.2085(3) 0.1586(2) 0.0388(9) Uani 1 1 d . . . C17 C -0.8595(5) -1.2175(3) 0.2427(3) 0.0524(11) Uani 1 1 d . . . H17 H -0.7780 -1.2051 0.2820 0.063 Uiso 1 1 calc R . . C18 C -1.0140(6) -1.2448(3) 0.2693(3) 0.0662(14) Uani 1 1 d . . . H18 H -1.0363 -1.2504 0.3262 0.079 Uiso 1 1 calc R . . C19 C -1.1343(5) -1.2637(3) 0.2115(4) 0.0683(15) Uani 1 1 d . . . H19 H -1.2381 -1.2826 0.2290 0.082 Uiso 1 1 calc R . . C20 C -1.1009(5) -1.2546(3) 0.1285(3) 0.0647(14) Uani 1 1 d . . . H20 H -1.1825 -1.2671 0.0892 0.078 Uiso 1 1 calc R . . C21 C -0.9468(5) -1.2270(3) 0.1018(3) 0.0508(11) Uani 1 1 d . . . H21 H -0.9257 -1.2210 0.0448 0.061 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 0.0721(3) 0.0642(3) 0.0745(3) 0.0268(3) -0.0094(3) 0.0100(3) O1 0.0415(14) 0.0412(17) 0.0394(16) 0.0000(14) 0.0071(12) 0.0001(13) O2 0.085(2) 0.091(3) 0.0385(18) -0.0064(18) 0.0172(16) -0.003(2) O3 0.0372(16) 0.065(2) 0.067(2) -0.0017(19) -0.0066(15) 0.0083(16) O4 0.0641(18) 0.0407(18) 0.071(2) 0.0180(16) -0.0152(16) -0.0076(15) N1 0.0422(18) 0.0328(19) 0.049(2) -0.0012(17) 0.0001(16) -0.0049(16) C1 0.035(2) 0.035(2) 0.048(3) 0.000(2) 0.002(2) -0.005(2) C2 0.035(2) 0.036(2) 0.029(2) -0.0039(19) 0.0015(17) -0.0014(18) C3 0.0279(19) 0.036(2) 0.034(2) 0.0015(19) 0.0058(17) 0.0032(18) C4 0.034(2) 0.042(3) 0.037(2) -0.001(2) 0.0070(18) -0.0020(19) C5 0.038(2) 0.059(3) 0.046(2) -0.006(2) -0.003(2) -0.007(2) C6 0.0406(19) 0.073(3) 0.035(2) 0.004(2) -0.007(2) 0.006(2) C7 0.038(2) 0.047(2) 0.043(2) 0.005(2) 0.0023(18) 0.005(2) C8 0.0327(18) 0.039(2) 0.043(2) -0.003(2) 0.0014(18) -0.0010(19) C9 0.0349(19) 0.032(2) 0.037(2) -0.0003(16) 0.0020(17) -0.0026(19) C10 0.041(2) 0.037(2) 0.046(3) 0.001(2) -0.0027(19) -0.0043(19) C11 0.056(3) 0.047(2) 0.040(2) 0.0038(18) -0.011(2) -0.001(2) C12 0.065(3) 0.039(2) 0.041(3) 0.001(2) 0.007(2) -0.010(2) C13 0.049(2) 0.066(3) 0.047(2) -0.006(2) 0.010(2) 0.007(3) C14 0.056(3) 0.073(4) 0.095(4) -0.007(3) -0.032(3) 0.011(3) C15 0.061(3) 0.036(3) 0.052(3) -0.010(2) 0.002(2) -0.003(2) C16 0.040(2) 0.028(2) 0.049(2) 0.000(2) 0.0034(18) -0.0054(19) C17 0.063(3) 0.043(3) 0.051(3) 0.002(2) -0.004(2) -0.010(2) C18 0.083(3) 0.057(3) 0.058(3) 0.004(3) 0.018(3) -0.012(3) C19 0.049(3) 0.060(3) 0.096(4) 0.008(3) 0.015(3) -0.010(2) C20 0.049(3) 0.059(3) 0.087(4) -0.001(3) -0.017(3) -0.011(2) C21 0.062(2) 0.045(3) 0.046(3) -0.001(2) -0.005(2) -0.008(2) _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 C7 1.905(4) . ? O1 C2 1.446(4) . ? O1 C12 1.375(4) . ? O2 C12 1.213(4) . ? O3 C10 1.346(4) . ? O3 C14 1.437(4) . ? O4 C1 1.205(4) . ? N1 C1 1.370(4) . ? N1 C4 1.408(5) . ? N1 C15 1.465(4) . ? C1 C2 1.560(5) . ? C2 C3 1.502(5) . ? C2 C9 1.541(5) . ? C3 C4 1.392(5) . ? C3 C8 1.382(5) . ? C4 C5 1.380(5) . ? C5 H5 0.9300 . ? C5 C6 1.395(5) . ? C6 H6 0.9300 . ? C6 C7 1.374(5) . ? C7 C8 1.384(5) . ? C8 H8 0.9300 . ? C9 H9 0.9800 . ? C9 C10 1.496(5) . ? C9 C13 1.524(4) . ? C10 C11 1.329(5) . ? C11 H11 0.9300 . ? C11 C12 1.427(6) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C15 C16 1.514(5) . ? C16 C17 1.377(5) . ? C16 C21 1.368(5) . ? C17 H17 0.9300 . ? C17 C18 1.383(5) . ? C18 H18 0.9300 . ? C18 C19 1.372(6) . ? C19 H19 0.9300 . ? C19 C20 1.359(6) . ? C20 H20 0.9300 . ? C20 C21 1.381(5) . ? C21 H21 0.9300 . ? 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 O1 C2 119.1(3) . . ? C10 O3 C14 116.9(3) . . ? C1 N1 C4 111.8(3) . . ? C1 N1 C15 122.6(4) . . ? C4 N1 C15 125.6(3) . . ? O4 C1 N1 126.6(4) . . ? O4 C1 C2 126.8(3) . . ? N1 C1 C2 106.6(3) . . ? O1 C2 C1 109.4(3) . . ? O1 C2 C3 107.8(3) . . ? O1 C2 C9 111.6(3) . . ? C3 C2 C1 102.6(3) . . ? C3 C2 C9 113.2(3) . . ? C9 C2 C1 111.8(3) . . ? C4 C3 C2 108.7(3) . . ? C8 C3 C2 130.5(3) . . ? C8 C3 C4 120.8(3) . . ? C3 C4 N1 109.8(3) . . ? C5 C4 N1 128.7(4) . . ? C5 C4 C3 121.5(4) . . ? C4 C5 H5 121.2 . . ? C4 C5 C6 117.7(4) . . ? C6 C5 H5 121.2 . . ? C5 C6 H6 119.9 . . ? C7 C6 C5 120.2(3) . . ? C7 C6 H6 119.9 . . ? C6 C7 Br1 119.1(3) . . ? C6 C7 C8 122.5(4) . . ? C8 C7 Br1 118.3(3) . . ? C3 C8 C7 117.2(4) . . ? C3 C8 H8 121.4 . . ? C7 C8 H8 121.4 . . ? C2 C9 H9 107.1 . . ? C10 C9 C2 109.2(3) . . ? C10 C9 H9 107.1 . . ? C10 C9 C13 114.4(3) . . ? C13 C9 C2 111.6(3) . . ? C13 C9 H9 107.1 . . ? O3 C10 C9 112.1(3) . . ? C11 C10 O3 126.1(4) . . ? C11 C10 C9 121.6(3) . . ? C10 C11 H11 119.3 . . ? C10 C11 C12 121.3(4) . . ? C12 C11 H11 119.3 . . ? O1 C12 C11 119.0(4) . . ? O2 C12 O1 115.5(4) . . ? O2 C12 C11 125.5(4) . . ? C9 C13 H13A 109.5 . . ? C9 C13 H13B 109.5 . . ? C9 C13 H13C 109.5 . . ? H13A C13 H13B 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O3 C14 H14A 109.5 . . ? O3 C14 H14B 109.5 . . ? O3 C14 H14C 109.5 . . ? H14A C14 H14B 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N1 C15 H15A 108.7 . . ? N1 C15 H15B 108.7 . . ? N1 C15 C16 114.2(3) . . ? H15A C15 H15B 107.6 . . ? C16 C15 H15A 108.7 . . ? C16 C15 H15B 108.7 . . ? C17 C16 C15 119.4(3) . . ? C21 C16 C15 121.8(3) . . ? C21 C16 C17 118.8(3) . . ? C16 C17 H17 119.7 . . ? C16 C17 C18 120.7(4) . . ? C18 C17 H17 119.7 . . ? C17 C18 H18 120.1 . . ? C19 C18 C17 119.8(4) . . ? C19 C18 H18 120.1 . . ? C18 C19 H19 120.2 . . ? C20 C19 C18 119.6(4) . . ? C20 C19 H19 120.2 . . ? C19 C20 H20 119.7 . . ? C19 C20 C21 120.6(4) . . ? C21 C20 H20 119.7 . . ? C16 C21 C20 120.5(4) . . ? C16 C21 H21 119.8 . . ? C20 C21 H21 119.8 . . ? _database_code_depnum_ccdc_archive 'CCDC 959984'