# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_111227-zl _database_code_depnum_ccdc_archive 'CCDC 876924' #TrackingRef '111227-zl.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C7 H6 Br N O' _chemical_formula_weight 200.04 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' Br Br -0.2901 2.4595 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 6.1832(7) _cell_length_b 4.7807(6) _cell_length_c 25.509(5) _cell_angle_alpha 90.00 _cell_angle_beta 94.353(15) _cell_angle_gamma 90.00 _cell_volume 751.87(19) _cell_formula_units_Z 4 _cell_measurement_temperature 290(2) _cell_measurement_reflns_used 2275 _cell_measurement_theta_min 3.1972 _cell_measurement_theta_max 29.0692 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.767 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 392 _exptl_absorpt_coefficient_mu 5.393 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1952 _exptl_absorpt_correction_T_max 0.2216 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 290(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Gemini S Ultra, Oxford Diffraction' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 15.9149 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5391 _diffrn_reflns_av_R_equivalents 0.0300 _diffrn_reflns_av_sigmaI/netI 0.0285 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 3.20 _diffrn_reflns_theta_max 26.36 _reflns_number_total 1528 _reflns_number_gt 1294 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlisPro (Oxford Diffraction Ltd.)' _computing_cell_refinement 'CrysAlisPro (Oxford Diffraction Ltd.)' _computing_data_reduction 'CrysAlisPro (Oxford Diffraction Ltd.)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 (L. J. Farrugia, 2001)' _computing_publication_material SHELXL-97 _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^)+(0.0333P)^2^+0.3088P] 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 1528 _refine_ls_number_parameters 92 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0381 _refine_ls_R_factor_gt 0.0292 _refine_ls_wR_factor_ref 0.0718 _refine_ls_wR_factor_gt 0.0670 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.90674(5) 0.35709(6) 0.298589(12) 0.05192(14) Uani 1 1 d . . . C1 C 0.7363(4) 0.6040(5) 0.33657(11) 0.0405(6) Uani 1 1 d . . . O1 O 0.2529(4) 1.4813(5) 0.47287(10) 0.0691(7) Uani 1 1 d . . . H1 H 0.3007 1.5680 0.4990 0.104 Uiso 1 1 calc R . . C4 C 0.4866(4) 0.9720(6) 0.38961(11) 0.0430(6) Uani 1 1 d . . . C7 C 0.3487(5) 1.1665(6) 0.41558(13) 0.0498(7) Uani 1 1 d . . . H7 H 0.2047 1.1857 0.4026 0.060 Uiso 1 1 calc R . . C2 C 0.5318(5) 0.6724(6) 0.31535(12) 0.0488(7) Uani 1 1 d . . . H2 H 0.4779 0.5962 0.2835 0.059 Uiso 1 1 calc R . . N1 N 0.4166(4) 1.3104(5) 0.45501(10) 0.0511(6) Uani 1 1 d . . . C5 C 0.6922(5) 0.8947(6) 0.41001(12) 0.0474(7) Uani 1 1 d . . . H5 H 0.7469 0.9694 0.4420 0.057 Uiso 1 1 calc R . . C6 C 0.8165(4) 0.7112(6) 0.38414(12) 0.0472(7) Uani 1 1 d . . . H6 H 0.9534 0.6596 0.3986 0.057 Uiso 1 1 calc R . . C3 C 0.4089(5) 0.8549(6) 0.34205(13) 0.0501(7) Uani 1 1 d . . . H3 H 0.2704 0.9013 0.3280 0.060 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 0.05215(19) 0.0535(2) 0.0503(2) -0.00228(14) 0.00461(14) 0.00797(13) C1 0.0445(14) 0.0389(15) 0.0382(16) 0.0024(12) 0.0034(12) 0.0007(11) O1 0.0694(14) 0.0801(16) 0.0567(16) -0.0210(13) -0.0022(12) 0.0284(13) C4 0.0472(15) 0.0395(15) 0.0415(17) 0.0010(13) -0.0015(12) 0.0007(12) C7 0.0490(15) 0.0524(17) 0.0471(19) -0.0030(14) -0.0023(13) 0.0077(13) C2 0.0500(15) 0.0520(18) 0.0422(17) -0.0060(13) -0.0107(13) 0.0037(13) N1 0.0564(14) 0.0507(15) 0.0456(16) -0.0065(12) 0.0007(12) 0.0149(11) C5 0.0495(15) 0.0478(17) 0.0429(17) -0.0002(13) -0.0084(13) 0.0006(12) C6 0.0420(14) 0.0513(17) 0.0466(18) 0.0001(14) -0.0068(12) 0.0050(13) C3 0.0439(15) 0.0524(17) 0.0513(19) -0.0077(14) -0.0126(13) 0.0080(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C1 1.897(3) . ? C1 C6 1.375(4) . ? C1 C2 1.377(4) . ? O1 N1 1.404(3) . ? O1 H1 0.8200 . ? C4 C5 1.387(4) . ? C4 C3 1.388(4) . ? C4 C7 1.455(4) . ? C7 N1 1.264(4) . ? C7 H7 0.9300 . ? C2 C3 1.371(4) . ? C2 H2 0.9300 . ? C5 C6 1.369(4) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C3 H3 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 C6 C1 C2 121.2(3) . . ? C6 C1 Br1 120.4(2) . . ? C2 C1 Br1 118.5(2) . . ? N1 O1 H1 109.5 . . ? C5 C4 C3 117.8(3) . . ? C5 C4 C7 123.5(3) . . ? C3 C4 C7 118.7(3) . . ? N1 C7 C4 122.6(3) . . ? N1 C7 H7 118.7 . . ? C4 C7 H7 118.7 . . ? C3 C2 C1 118.9(3) . . ? C3 C2 H2 120.6 . . ? C1 C2 H2 120.6 . . ? C7 N1 O1 111.8(2) . . ? C6 C5 C4 121.5(3) . . ? C6 C5 H5 119.3 . . ? C4 C5 H5 119.3 . . ? C5 C6 C1 119.1(3) . . ? C5 C6 H6 120.4 . . ? C1 C6 H6 120.4 . . ? C2 C3 C4 121.5(3) . . ? C2 C3 H3 119.2 . . ? C4 C3 H3 119.2 . . ? 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 C5 C4 C7 N1 10.2(5) . . . . ? C3 C4 C7 N1 -170.3(3) . . . . ? C6 C1 C2 C3 1.2(4) . . . . ? Br1 C1 C2 C3 -178.8(2) . . . . ? C4 C7 N1 O1 -179.9(3) . . . . ? C3 C4 C5 C6 0.6(4) . . . . ? C7 C4 C5 C6 -179.9(3) . . . . ? C4 C5 C6 C1 0.8(5) . . . . ? C2 C1 C6 C5 -1.7(4) . . . . ? Br1 C1 C6 C5 178.2(2) . . . . ? C1 C2 C3 C4 0.3(5) . . . . ? C5 C4 C3 C2 -1.1(5) . . . . ? C7 C4 C3 C2 179.3(3) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.36 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.362 _refine_diff_density_min -0.374 _refine_diff_density_rms 0.062