# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_global # Attachment '- polymorph I.cif' data_c:\determination\solution\c64-\khc64-85k-2 #TrackingRef '- polymorph I.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H8 Br N3 O' _chemical_formula_sum 'C11 H8 Br N3 O' _chemical_formula_weight 278.10 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.0863(5) _cell_length_b 10.9647(4) _cell_length_c 18.8209(9) _cell_angle_alpha 90.00 _cell_angle_beta 92.043(4) _cell_angle_gamma 90.00 _cell_volume 2080.14(16) _cell_formula_units_Z 8 _cell_measurement_temperature 85(2) _cell_measurement_reflns_used 14176 _cell_measurement_theta_min 2.15 _cell_measurement_theta_max 29.16 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.776 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1104 _exptl_absorpt_coefficient_mu 3.932 _exptl_absorpt_correction_type Numerical _exptl_absorpt_correction_T_min 0.322 _exptl_absorpt_correction_T_max 0.375 _exptl_absorpt_process_details 'shape of crystal determined optically' _exptl_special_details ; ? ; _diffrn_ambient_temperature 85(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 'STOE IPDS IIT' _diffrn_measurement_method 'rotation method' _diffrn_detector_area_resol_mean '0.15 mm' _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14176 _diffrn_reflns_av_R_equivalents 0.0753 _diffrn_reflns_av_sigmaI/netI 0.0653 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 29.16 _reflns_number_total 5576 _reflns_number_gt 4384 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'X-Area 1.31 (Stoe & Cie GmbH, 2005)' _computing_cell_refinement 'X-Area 1.31 (Stoe & Cie GmbH, 2005)' _computing_data_reduction 'X-Area 1.31 (Stoe & Cie GmbH, 2005)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX (Farrugia, 1999)' _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^)+(0.0432P)^2^+4.3686P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5576 _refine_ls_number_parameters 289 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0831 _refine_ls_R_factor_gt 0.0591 _refine_ls_wR_factor_ref 0.1196 _refine_ls_wR_factor_gt 0.1117 _refine_ls_goodness_of_fit_ref 1.153 _refine_ls_restrained_S_all 1.153 _refine_ls_shift/su_max 0.009 _refine_ls_shift/su_mean 0.001 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 C1 C 1.4499(4) 0.0421(4) -0.0878(2) 0.0135(8) Uani 1 1 d . . . H1 H 1.5005 -0.0272 -0.0956 0.016 Uiso 1 1 calc R . . C2 C 1.4794(4) 0.1477(4) -0.1234(2) 0.0139(8) Uani 1 1 d . . . H2 H 1.5512 0.1482 -0.1531 0.017 Uiso 1 1 calc R . . C3 C 1.3059(4) 0.2430(4) -0.0735(2) 0.0162(8) Uani 1 1 d . . . H3 H 1.2513 0.3106 -0.0687 0.019 Uiso 1 1 calc R . . C4 C 1.2791(4) 0.1375(4) -0.0354(2) 0.0132(8) Uani 1 1 d . . . C5 C 1.1694(4) 0.1399(4) 0.0172(2) 0.0131(8) Uani 1 1 d . . . C6 C 1.0544(4) 0.0084(4) 0.1025(2) 0.0132(8) Uani 1 1 d . . . C7 C 0.9532(4) 0.0886(4) 0.1183(2) 0.0126(7) Uani 1 1 d . . . H7 H 0.9441 0.1629 0.0948 0.015 Uiso 1 1 calc R . . C8 C 0.8658(4) 0.0549(4) 0.1704(2) 0.0119(7) Uani 1 1 d . . . C9 C 0.8721(4) -0.0553(4) 0.2054(2) 0.0168(8) Uani 1 1 d . . . H9 H 0.8108 -0.0758 0.2392 0.020 Uiso 1 1 calc R . . C10 C 0.9736(4) -0.1347(4) 0.1885(3) 0.0181(9) Uani 1 1 d . . . H10 H 0.9807 -0.2094 0.2117 0.022 Uiso 1 1 calc R . . C11 C 1.0649(4) -0.1047(4) 0.1374(2) 0.0168(8) Uani 1 1 d . . . H11 H 1.1322 -0.1589 0.1266 0.020 Uiso 1 1 calc R . . C12 C 1.7939(4) 0.4549(4) 0.0106(2) 0.0173(8) Uani 1 1 d . . . H12 H 1.8503 0.5213 0.0061 0.021 Uiso 1 1 calc R . . C13 C 1.8259(4) 0.3457(4) -0.0215(2) 0.0152(8) Uani 1 1 d . . . H13 H 1.9035 0.3411 -0.0466 0.018 Uiso 1 1 calc R . . C14 C 1.6395(4) 0.2590(4) 0.0198(2) 0.0157(8) Uani 1 1 d . . . H14 H 1.5828 0.1927 0.0238 0.019 Uiso 1 1 calc R . . C15 C 1.6083(4) 0.3687(4) 0.0531(2) 0.0133(8) Uani 1 1 d . . . C16 C 1.4859(4) 0.3742(4) 0.0971(2) 0.0142(8) Uani 1 1 d . . . C17 C 1.3531(4) 0.5156(4) 0.1671(2) 0.0123(7) Uani 1 1 d . . . C18 C 1.2320(4) 0.4556(4) 0.1589(2) 0.0132(8) Uani 1 1 d . . . H18 H 1.2203 0.3929 0.1261 0.016 Uiso 1 1 calc R . . C19 C 1.1291(4) 0.4921(4) 0.2013(2) 0.0148(8) Uani 1 1 d . . . C20 C 1.1420(4) 0.5838(4) 0.2515(2) 0.0152(8) Uani 1 1 d . . . H20 H 1.0718 0.6047 0.2798 0.018 Uiso 1 1 calc R . . C21 C 1.2632(4) 0.6438(4) 0.2583(2) 0.0151(8) Uani 1 1 d . . . H21 H 1.2740 0.7067 0.2911 0.018 Uiso 1 1 calc R . . C22 C 1.3690(4) 0.6105(4) 0.2163(2) 0.0129(8) Uani 1 1 d . . . H22 H 1.4496 0.6513 0.2211 0.015 Uiso 1 1 calc R . . N1 N 1.3506(3) 0.0353(3) -0.0420(2) 0.0134(7) Uani 1 1 d . . . N2 N 1.4081(3) 0.2498(3) -0.1169(2) 0.0169(7) Uani 1 1 d . . . N3 N 1.1487(3) 0.0320(3) 0.05057(19) 0.0121(7) Uani 1 1 d . . . H3B H 1.1981 -0.0281 0.0389 0.014 Uiso 1 1 calc R . . N4 N 1.6842(3) 0.4680(3) 0.0482(2) 0.0147(7) Uani 1 1 d . . . N5 N 1.7495(4) 0.2469(3) -0.0178(2) 0.0166(7) Uani 1 1 d . . . N6 N 1.4621(3) 0.4857(3) 0.12520(19) 0.0122(7) Uani 1 1 d . . . H6 H 1.5178 0.5428 0.1168 0.015 Uiso 1 1 calc R . . O1 O 1.1076(3) 0.2349(3) 0.02629(18) 0.0187(6) Uani 1 1 d . . . O2 O 1.4173(3) 0.2833(3) 0.10437(19) 0.0199(7) Uani 1 1 d . . . Br1 Br 0.73174(4) 0.16789(4) 0.19605(2) 0.01567(11) Uani 1 1 d . . . Br2 Br 0.96317(4) 0.41077(4) 0.18763(3) 0.01954(12) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0143(17) 0.0135(19) 0.013(2) -0.0035(15) 0.0032(14) -0.0014(14) C2 0.0145(17) 0.013(2) 0.014(2) -0.0013(15) 0.0039(14) -0.0023(14) C3 0.0170(18) 0.0116(19) 0.020(2) -0.0016(17) 0.0037(16) -0.0021(15) C4 0.0142(17) 0.0094(18) 0.016(2) -0.0023(15) 0.0024(14) -0.0023(14) C5 0.0158(17) 0.0096(18) 0.014(2) -0.0042(15) 0.0031(14) -0.0008(14) C6 0.0166(18) 0.0117(18) 0.0115(19) 0.0004(15) 0.0050(14) -0.0031(15) C7 0.0149(17) 0.0125(18) 0.0105(18) -0.0012(15) 0.0014(14) -0.0009(15) C8 0.0118(16) 0.0114(18) 0.0128(19) -0.0023(15) 0.0038(14) 0.0008(14) C9 0.0200(19) 0.014(2) 0.017(2) 0.0024(16) 0.0060(16) 0.0012(15) C10 0.022(2) 0.0102(18) 0.022(2) 0.0045(17) 0.0069(17) 0.0014(15) C11 0.0186(19) 0.013(2) 0.019(2) 0.0026(16) 0.0096(16) 0.0028(15) C12 0.0197(19) 0.013(2) 0.019(2) -0.0007(17) 0.0028(16) -0.0026(16) C13 0.0148(17) 0.014(2) 0.017(2) -0.0001(16) 0.0052(15) 0.0029(15) C14 0.0196(19) 0.0118(19) 0.016(2) -0.0009(16) 0.0051(15) 0.0002(15) C15 0.0135(17) 0.0145(19) 0.012(2) 0.0019(15) 0.0025(14) 0.0017(14) C16 0.0183(18) 0.0121(19) 0.012(2) 0.0008(15) 0.0039(15) -0.0013(15) C17 0.0145(17) 0.0102(18) 0.0124(19) 0.0019(15) 0.0017(14) 0.0004(14) C18 0.0169(18) 0.0088(18) 0.014(2) 0.0012(15) 0.0016(15) 0.0006(14) C19 0.0127(17) 0.014(2) 0.017(2) 0.0027(16) 0.0020(15) -0.0015(14) C20 0.0183(18) 0.0142(19) 0.013(2) 0.0019(16) 0.0027(15) 0.0047(16) C21 0.0219(19) 0.0076(19) 0.016(2) -0.0015(15) 0.0030(16) 0.0003(15) C22 0.0165(18) 0.0074(18) 0.015(2) -0.0006(15) 0.0019(14) 0.0006(14) N1 0.0156(15) 0.0113(16) 0.0136(17) 0.0011(13) 0.0035(13) -0.0003(13) N2 0.0198(17) 0.0120(16) 0.0192(19) -0.0006(15) 0.0050(14) -0.0044(14) N3 0.0147(15) 0.0087(16) 0.0131(17) -0.0025(13) 0.0055(13) -0.0008(12) N4 0.0158(15) 0.0123(17) 0.0162(18) 0.0009(14) 0.0032(13) 0.0010(13) N5 0.0202(16) 0.0125(16) 0.0175(19) 0.0004(15) 0.0062(14) 0.0015(14) N6 0.0142(15) 0.0109(16) 0.0118(17) -0.0009(13) 0.0037(12) -0.0006(12) O1 0.0224(15) 0.0137(15) 0.0204(17) -0.0003(13) 0.0072(12) 0.0001(12) O2 0.0212(14) 0.0087(14) 0.0303(19) -0.0010(13) 0.0097(13) -0.0025(12) Br1 0.01440(18) 0.01305(19) 0.0199(2) -0.00196(17) 0.00604(14) 0.00098(15) Br2 0.01452(19) 0.0231(2) 0.0213(2) -0.00487(18) 0.00464(15) -0.00313(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 C1 N1 1.346(5) . ? C1 C2 1.377(6) . ? C1 H1 0.9300 . ? C2 N2 1.339(5) . ? C2 H2 0.9300 . ? C3 N2 1.340(5) . ? C3 C4 1.392(6) . ? C3 H3 0.9300 . ? C4 N1 1.341(5) . ? C4 C5 1.510(5) . ? C5 O1 1.229(5) . ? C5 N3 1.360(5) . ? C6 C7 1.388(5) . ? C6 C11 1.406(6) . ? C6 N3 1.411(5) . ? C7 C8 1.391(5) . ? C7 H7 0.9300 . ? C8 C9 1.377(6) . ? C8 Br1 1.909(4) . ? C9 C10 1.389(6) . ? C9 H9 0.9300 . ? C10 C11 1.394(6) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 N4 1.341(5) . ? C12 C13 1.385(6) . ? C12 H12 0.9300 . ? C13 N5 1.332(6) . ? C13 H13 0.9300 . ? C14 N5 1.343(5) . ? C14 C15 1.398(6) . ? C14 H14 0.9300 . ? C15 N4 1.336(5) . ? C15 C16 1.513(5) . ? C16 O2 1.223(5) . ? C16 N6 1.357(5) . ? C17 C18 1.391(5) . ? C17 C22 1.397(6) . ? C17 N6 1.414(5) . ? C18 C19 1.390(5) . ? C18 H18 0.9300 . ? C19 C20 1.383(6) . ? C19 Br2 1.905(4) . ? C20 C21 1.390(6) . ? C20 H20 0.9300 . ? C21 C22 1.399(5) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? N3 H3B 0.8600 . ? N6 H6 0.8600 . ? 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 N1 C1 C2 122.5(4) . . ? N1 C1 H1 118.7 . . ? C2 C1 H1 118.7 . . ? N2 C2 C1 122.2(4) . . ? N2 C2 H2 118.9 . . ? C1 C2 H2 118.9 . . ? N2 C3 C4 121.9(4) . . ? N2 C3 H3 119.1 . . ? C4 C3 H3 119.1 . . ? N1 C4 C3 122.1(4) . . ? N1 C4 C5 119.0(4) . . ? C3 C4 C5 118.8(4) . . ? O1 C5 N3 125.9(4) . . ? O1 C5 C4 119.6(4) . . ? N3 C5 C4 114.5(3) . . ? C7 C6 C11 120.1(4) . . ? C7 C6 N3 123.5(4) . . ? C11 C6 N3 116.4(4) . . ? C6 C7 C8 118.2(4) . . ? C6 C7 H7 120.9 . . ? C8 C7 H7 120.9 . . ? C9 C8 C7 123.4(4) . . ? C9 C8 Br1 118.0(3) . . ? C7 C8 Br1 118.6(3) . . ? C8 C9 C10 117.5(4) . . ? C8 C9 H9 121.3 . . ? C10 C9 H9 121.3 . . ? C9 C10 C11 121.4(4) . . ? C9 C10 H10 119.3 . . ? C11 C10 H10 119.3 . . ? C10 C11 C6 119.4(4) . . ? C10 C11 H11 120.3 . . ? C6 C11 H11 120.3 . . ? N4 C12 C13 122.1(4) . . ? N4 C12 H12 118.9 . . ? C13 C12 H12 118.9 . . ? N5 C13 C12 122.4(4) . . ? N5 C13 H13 118.8 . . ? C12 C13 H13 118.8 . . ? N5 C14 C15 121.6(4) . . ? N5 C14 H14 119.2 . . ? C15 C14 H14 119.2 . . ? N4 C15 C14 122.1(4) . . ? N4 C15 C16 119.1(4) . . ? C14 C15 C16 118.7(4) . . ? O2 C16 N6 125.6(4) . . ? O2 C16 C15 120.3(4) . . ? N6 C16 C15 114.1(4) . . ? C18 C17 C22 120.3(4) . . ? C18 C17 N6 121.7(4) . . ? C22 C17 N6 118.0(4) . . ? C19 C18 C17 118.1(4) . . ? C19 C18 H18 120.9 . . ? C17 C18 H18 120.9 . . ? C20 C19 C18 123.1(4) . . ? C20 C19 Br2 119.6(3) . . ? C18 C19 Br2 117.3(3) . . ? C19 C20 C21 117.9(4) . . ? C19 C20 H20 121.0 . . ? C21 C20 H20 121.0 . . ? C20 C21 C22 120.7(4) . . ? C20 C21 H21 119.7 . . ? C22 C21 H21 119.7 . . ? C17 C22 C21 119.8(4) . . ? C17 C22 H22 120.1 . . ? C21 C22 H22 120.1 . . ? C4 N1 C1 115.4(4) . . ? C2 N2 C3 115.9(4) . . ? C5 N3 C6 126.7(3) . . ? C5 N3 H3B 116.6 . . ? C6 N3 H3B 116.6 . . ? C15 N4 C12 115.7(4) . . ? C13 N5 C14 115.9(4) . . ? C16 N6 C17 125.3(4) . . ? C16 N6 H6 117.3 . . ? C17 N6 H6 117.3 . . ? 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 N1 C1 C2 N2 -2.4(7) . . . . ? N2 C3 C4 N1 -2.7(7) . . . . ? N2 C3 C4 C5 174.9(4) . . . . ? N1 C4 C5 O1 176.4(4) . . . . ? C3 C4 C5 O1 -1.3(6) . . . . ? N1 C4 C5 N3 -3.8(6) . . . . ? C3 C4 C5 N3 178.5(4) . . . . ? C11 C6 C7 C8 1.4(6) . . . . ? N3 C6 C7 C8 179.7(4) . . . . ? C6 C7 C8 C9 -1.9(7) . . . . ? C6 C7 C8 Br1 176.9(3) . . . . ? C7 C8 C9 C10 1.5(7) . . . . ? Br1 C8 C9 C10 -177.3(3) . . . . ? C8 C9 C10 C11 -0.6(7) . . . . ? C9 C10 C11 C6 0.1(7) . . . . ? C7 C6 C11 C10 -0.5(7) . . . . ? N3 C6 C11 C10 -178.9(4) . . . . ? N4 C12 C13 N5 0.6(7) . . . . ? N5 C14 C15 N4 1.4(7) . . . . ? N5 C14 C15 C16 -177.5(4) . . . . ? N4 C15 C16 O2 -177.5(4) . . . . ? C14 C15 C16 O2 1.4(6) . . . . ? N4 C15 C16 N6 3.1(6) . . . . ? C14 C15 C16 N6 -178.0(4) . . . . ? C22 C17 C18 C19 -0.6(6) . . . . ? N6 C17 C18 C19 -178.8(4) . . . . ? C17 C18 C19 C20 -0.8(7) . . . . ? C17 C18 C19 Br2 178.7(3) . . . . ? C18 C19 C20 C21 1.6(7) . . . . ? Br2 C19 C20 C21 -177.9(3) . . . . ? C19 C20 C21 C22 -1.1(6) . . . . ? C18 C17 C22 C21 1.1(6) . . . . ? N6 C17 C22 C21 179.3(4) . . . . ? C20 C21 C22 C17 -0.3(6) . . . . ? C3 C4 N1 C1 0.2(6) . . . . ? C5 C4 N1 C1 -177.4(4) . . . . ? C2 C1 N1 C4 2.2(6) . . . . ? C1 C2 N2 C3 -0.1(6) . . . . ? C4 C3 N2 C2 2.5(6) . . . . ? O1 C5 N3 C6 -1.0(7) . . . . ? C4 C5 N3 C6 179.2(4) . . . . ? C7 C6 N3 C5 11.3(7) . . . . ? C11 C6 N3 C5 -170.4(4) . . . . ? C14 C15 N4 C12 -1.5(6) . . . . ? C16 C15 N4 C12 177.4(4) . . . . ? C13 C12 N4 C15 0.5(7) . . . . ? C12 C13 N5 C14 -0.7(7) . . . . ? C15 C14 N5 C13 -0.3(6) . . . . ? O2 C16 N6 C17 -0.6(7) . . . . ? C15 C16 N6 C17 178.8(4) . . . . ? C18 C17 N6 C16 -29.2(6) . . . . ? C22 C17 N6 C16 152.6(4) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 29.16 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.940 _refine_diff_density_min -1.003 _refine_diff_density_rms 0.139 _database_code_depnum_ccdc_archive 'CCDC 817124' ####################################################################### # # 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_global # Attachment '3Br(polymorph).cif' data_e:\measurement\c63\khc63-85k #TrackingRef '3Br(polymorph).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C H Br N O' _chemical_formula_weight 122.94 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' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 3.8163(6) _cell_length_b 22.850(3) _cell_length_c 11.918(2) _cell_angle_alpha 90.00 _cell_angle_beta 92.724(13) _cell_angle_gamma 90.00 _cell_volume 1038.1(3) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 0.197 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 57 _exptl_absorpt_coefficient_mu 0.969 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11155 _diffrn_reflns_av_R_equivalents 0.1286 _diffrn_reflns_av_sigmaI/netI 0.0669 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.47 _diffrn_reflns_theta_max 29.18 _reflns_number_total 2785 _reflns_number_gt 2468 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0591P)^2^+1.4734P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2785 _refine_ls_number_parameters 177 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0558 _refine_ls_R_factor_gt 0.0486 _refine_ls_wR_factor_ref 0.1265 _refine_ls_wR_factor_gt 0.1216 _refine_ls_goodness_of_fit_ref 1.090 _refine_ls_restrained_S_all 1.090 _refine_ls_shift/su_max 0.369 _refine_ls_shift/su_mean 0.039 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 0.24764(8) 0.396101(13) 0.09411(3) 0.01926(13) Uani 1 1 d . . . N2 N 0.3931(8) 0.82579(13) 0.1213(2) 0.0243(6) Uani 1 1 d . . . O1 O 0.0296(7) 0.68411(11) 0.3044(2) 0.0236(5) Uani 1 1 d . . . N1 N 0.4691(8) 0.70941(12) 0.0509(2) 0.0198(5) Uani 1 1 d . . . C8 C 0.1283(8) 0.46169(14) 0.1836(3) 0.0176(6) Uani 1 1 d . . . C2 C 0.5368(10) 0.81201(15) 0.0240(3) 0.0242(7) Uani 1 1 d . . . H5 H 0.622(11) 0.846(2) -0.022(3) 0.028(11) Uiso 1 1 d . . . C5 C 0.1786(8) 0.67422(14) 0.2171(3) 0.0188(6) Uani 1 1 d . . . C4 C 0.3216(8) 0.72293(14) 0.1478(3) 0.0182(6) Uani 1 1 d . . . C7 C 0.2087(9) 0.51711(14) 0.1462(3) 0.0176(6) Uani 1 1 d . . . H2 H 0.333(12) 0.525(2) 0.077(3) 0.023(10) Uiso 1 1 d . . . N3 N 0.2325(8) 0.62047(13) 0.1726(2) 0.0192(5) Uani 1 1 d . . . H4 H 0.343(15) 0.621(3) 0.118(5) 0.046(15) Uiso 1 1 d . . . C6 C 0.1362(9) 0.56542(13) 0.2135(3) 0.0181(6) Uani 1 1 d . . . C3 C 0.2839(9) 0.78102(15) 0.1832(3) 0.0218(7) Uani 1 1 d . . . H8 H 0.198(13) 0.790(2) 0.256(4) 0.038(13) Uiso 1 1 d . . . C9 C -0.0313(9) 0.45226(15) 0.2851(3) 0.0200(6) Uani 1 1 d . . . H1 H -0.094(11) 0.4113(19) 0.311(3) 0.014(9) Uiso 1 1 d . . . C10 C -0.1052(9) 0.50068(15) 0.3491(3) 0.0199(6) Uani 1 1 d . . . H3 H -0.233(10) 0.495(2) 0.423(3) 0.022(11) Uiso 1 1 d . . . C1 C 0.5760(9) 0.75436(14) -0.0096(3) 0.0215(6) Uani 1 1 d . . . H7 H 0.690(13) 0.746(2) -0.075(4) 0.032(12) Uiso 1 1 d . . . C11 C -0.0209(9) 0.55681(15) 0.3163(3) 0.0192(6) Uani 1 1 d . . . H6 H -0.067(14) 0.588(2) 0.357(4) 0.039(14) 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 Br1 0.0237(2) 0.01230(19) 0.02198(19) -0.00119(11) 0.00388(13) -0.00002(10) N2 0.0333(16) 0.0135(13) 0.0264(14) -0.0003(11) 0.0044(12) 0.0014(11) O1 0.0327(13) 0.0161(11) 0.0229(11) -0.0023(9) 0.0106(9) 0.0004(9) N1 0.0253(14) 0.0147(12) 0.0195(12) 0.0011(10) 0.0023(10) -0.0010(10) C8 0.0218(15) 0.0126(14) 0.0184(13) 0.0005(11) 0.0016(11) 0.0018(11) C2 0.0287(17) 0.0160(15) 0.0281(16) 0.0027(13) 0.0035(13) -0.0026(13) C5 0.0209(15) 0.0148(14) 0.0206(14) 0.0001(12) 0.0004(11) -0.0004(11) C4 0.0204(15) 0.0144(14) 0.0201(14) -0.0006(12) 0.0030(11) 0.0022(11) C7 0.0214(15) 0.0120(14) 0.0195(14) -0.0004(12) 0.0030(11) 0.0003(11) N3 0.0262(14) 0.0123(12) 0.0197(12) -0.0005(11) 0.0074(11) -0.0006(10) C6 0.0237(15) 0.0104(14) 0.0204(14) -0.0007(12) 0.0015(11) 0.0005(11) C3 0.0263(17) 0.0150(15) 0.0244(15) -0.0008(13) 0.0029(13) 0.0032(12) C9 0.0247(16) 0.0151(14) 0.0200(14) 0.0025(12) 0.0002(12) -0.0019(12) C10 0.0210(15) 0.0195(15) 0.0195(14) 0.0007(12) 0.0042(11) -0.0009(12) C1 0.0275(17) 0.0144(15) 0.0231(15) 0.0005(13) 0.0065(13) 0.0018(12) C11 0.0229(16) 0.0172(15) 0.0178(13) -0.0029(12) 0.0026(11) 0.0008(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 Br1 C8 1.907(3) . ? N2 C3 1.339(5) . ? N2 C2 1.344(4) . ? O1 C5 1.230(4) . ? N1 C1 1.330(4) . ? N1 C4 1.344(4) . ? C8 C7 1.382(4) . ? C8 C9 1.397(4) . ? C2 C1 1.387(5) . ? C5 N3 1.357(4) . ? C5 C4 1.504(4) . ? C4 C3 1.402(5) . ? C7 C6 1.400(4) . ? N3 C6 1.404(4) . ? C6 C11 1.404(4) . ? C9 C10 1.381(5) . ? C10 C11 1.383(5) . ? 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 C3 N2 C2 116.5(3) . . ? C1 N1 C4 116.1(3) . . ? C7 C8 C9 122.2(3) . . ? C7 C8 Br1 118.5(2) . . ? C9 C8 Br1 119.2(2) . . ? N2 C2 C1 121.7(3) . . ? O1 C5 N3 125.6(3) . . ? O1 C5 C4 121.5(3) . . ? N3 C5 C4 112.9(3) . . ? N1 C4 C3 121.9(3) . . ? N1 C4 C5 118.7(3) . . ? C3 C4 C5 119.3(3) . . ? C8 C7 C6 119.0(3) . . ? C5 N3 C6 128.9(3) . . ? C7 C6 C11 119.6(3) . . ? C7 C6 N3 116.5(3) . . ? C11 C6 N3 123.9(3) . . ? N2 C3 C4 121.2(3) . . ? C10 C9 C8 117.6(3) . . ? C9 C10 C11 122.0(3) . . ? N1 C1 C2 122.4(3) . . ? C10 C11 C6 119.4(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 C3 N2 C2 C1 -1.2(5) . . . . ? C1 N1 C4 C3 -0.3(5) . . . . ? C1 N1 C4 C5 176.9(3) . . . . ? O1 C5 C4 N1 -177.4(3) . . . . ? N3 C5 C4 N1 2.5(4) . . . . ? O1 C5 C4 C3 -0.1(5) . . . . ? N3 C5 C4 C3 179.7(3) . . . . ? C9 C8 C7 C6 1.7(5) . . . . ? Br1 C8 C7 C6 -177.3(2) . . . . ? O1 C5 N3 C6 -0.1(6) . . . . ? C4 C5 N3 C6 -180.0(3) . . . . ? C8 C7 C6 C11 -1.0(5) . . . . ? C8 C7 C6 N3 178.3(3) . . . . ? C5 N3 C6 C7 176.5(3) . . . . ? C5 N3 C6 C11 -4.3(6) . . . . ? C2 N2 C3 C4 0.5(5) . . . . ? N1 C4 C3 N2 0.2(5) . . . . ? C5 C4 C3 N2 -176.9(3) . . . . ? C7 C8 C9 C10 -0.7(5) . . . . ? Br1 C8 C9 C10 178.3(2) . . . . ? C8 C9 C10 C11 -1.1(5) . . . . ? C4 N1 C1 C2 -0.4(5) . . . . ? N2 C2 C1 N1 1.2(6) . . . . ? C9 C10 C11 C6 1.7(5) . . . . ? C7 C6 C11 C10 -0.7(5) . . . . ? N3 C6 C11 C10 -179.9(3) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 29.18 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 1.111 _refine_diff_density_min -1.397 _refine_diff_density_rms 0.157 _database_code_depnum_ccdc_archive 'CCDC 817125'