# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full J.Org.Chem. _journal_coden_cambridge 0035 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Harry Adams' _publ_contact_author_email h.adams@sheffield.ac.uk loop_ _publ_author_name 'Iain Coldham' A.Franklin 'Harry Adams' 'David Bensa' data_oic1m _database_code_depnum_ccdc_archive 'CCDC 791948' #TrackingRef 'OIC1M.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H13 N O3' _chemical_formula_sum 'C8 H13 N O3' _chemical_formula_weight 171.19 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1) _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 6.0046(14) _cell_length_b 6.1040(14) _cell_length_c 12.099(3) _cell_angle_alpha 90.00 _cell_angle_beta 103.144(4) _cell_angle_gamma 90.00 _cell_volume 431.83(17) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2328 _cell_measurement_theta_min 6.917 _cell_measurement_theta_max 54.642 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.317 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 184 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9685 _exptl_absorpt_correction_T_max 0.9802 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker smart1000ccd' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 100 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 4884 _diffrn_reflns_av_R_equivalents 0.0246 _diffrn_reflns_av_sigmaI/netI 0.0211 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 27.53 _reflns_number_total 1080 _reflns_number_gt 986 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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. The compound was enantiomerically pure, although there is no heavy atom to achive a sensible Flack parameter, ; _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^)+(0.0567P)^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 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 ? _chemical_absolute_configuration unk _refine_ls_number_reflns 1080 _refine_ls_number_parameters 109 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0360 _refine_ls_R_factor_gt 0.0319 _refine_ls_wR_factor_ref 0.0855 _refine_ls_wR_factor_gt 0.0832 _refine_ls_goodness_of_fit_ref 1.106 _refine_ls_restrained_S_all 1.106 _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 0.3831(3) 0.1901(3) 0.83126(15) 0.0297(4) Uani 1 1 d . . . H1A H 0.4850 0.2405 0.7957 0.036 Uiso 1 1 calc R . . O1 O 0.2123(2) -0.0450(2) 0.92196(11) 0.0275(3) Uani 1 1 d . . . O2 O 0.5503(2) -0.1415(3) 0.88630(12) 0.0359(4) Uani 1 1 d . . . O3 O -0.2818(2) 0.4955(3) 0.79891(11) 0.0298(3) Uani 1 1 d . . . H3A H -0.3378 0.6019 0.8273 0.045 Uiso 1 1 calc R . . C1 C 0.3986(3) -0.0061(3) 0.87963(15) 0.0239(4) Uani 1 1 d . . . C2 C 0.0667(3) 0.1471(3) 0.90683(15) 0.0235(4) Uani 1 1 d . . . H2A H 0.0542 0.2068 0.9813 0.028 Uiso 1 1 calc R . . H2B H -0.0885 0.1103 0.8624 0.028 Uiso 1 1 calc R . . C3 C 0.1818(3) 0.3152(3) 0.84225(14) 0.0209(4) Uani 1 1 d . . . H3B H 0.2313 0.4455 0.8918 0.025 Uiso 1 1 calc R . . C4 C 0.0445(3) 0.3920(3) 0.72599(15) 0.0211(4) Uani 1 1 d . . . H4A H 0.1572 0.4565 0.6857 0.025 Uiso 1 1 calc R . . C5 C -0.1205(3) 0.5743(3) 0.73768(15) 0.0223(4) Uani 1 1 d . . . H5A H -0.0348 0.6998 0.7785 0.027 Uiso 1 1 calc R . . H5B H -0.2020 0.6251 0.6615 0.027 Uiso 1 1 calc R . . C6 C -0.0765(3) 0.2040(3) 0.65056(16) 0.0260(4) Uani 1 1 d . . . H6A H 0.0255 0.0747 0.6600 0.031 Uiso 1 1 calc R . . H6B H -0.2168 0.1625 0.6755 0.031 Uiso 1 1 calc R . . C7 C -0.1392(3) 0.2677(3) 0.52739(15) 0.0303(4) Uani 1 1 d . . . H7A H -0.0177 0.2901 0.4902 0.036 Uiso 1 1 calc R . . C8 C -0.3489(4) 0.2948(4) 0.46706(17) 0.0426(6) Uani 1 1 d . . . H8C H -0.4751 0.2739 0.5012 0.051 Uiso 1 1 calc R . . H8A H -0.3743 0.3353 0.3894 0.051 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 0.0216(7) 0.0328(10) 0.0377(9) 0.0099(7) 0.0128(7) 0.0050(7) O1 0.0258(6) 0.0209(8) 0.0368(7) 0.0042(6) 0.0093(6) 0.0032(6) O2 0.0316(7) 0.0301(8) 0.0450(8) -0.0058(7) 0.0065(6) 0.0104(7) O3 0.0307(7) 0.0231(7) 0.0406(8) -0.0020(6) 0.0184(6) 0.0023(6) C1 0.0225(8) 0.0251(9) 0.0223(8) -0.0055(8) 0.0015(7) 0.0008(8) C2 0.0235(8) 0.0221(9) 0.0259(9) 0.0043(7) 0.0079(7) 0.0020(7) C3 0.0178(8) 0.0207(9) 0.0244(8) 0.0013(7) 0.0049(6) -0.0007(7) C4 0.0223(8) 0.0179(9) 0.0240(8) 0.0007(7) 0.0070(7) -0.0018(7) C5 0.0244(9) 0.0182(9) 0.0235(8) 0.0008(7) 0.0033(7) 0.0002(7) C6 0.0314(10) 0.0208(10) 0.0268(9) -0.0026(7) 0.0085(8) -0.0005(8) C7 0.0395(11) 0.0269(10) 0.0250(9) -0.0035(8) 0.0087(8) -0.0016(9) C8 0.0464(13) 0.0449(15) 0.0322(11) -0.0062(11) -0.0002(10) -0.0043(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 N1 C1 1.327(3) . ? N1 C3 1.461(2) . ? N1 H1A 0.8800 . ? O1 C1 1.353(2) . ? O1 C2 1.449(2) . ? O2 C1 1.219(2) . ? O3 C5 1.430(2) . ? O3 H3A 0.8400 . ? C2 C3 1.545(2) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.533(2) . ? C3 H3B 1.0000 . ? C4 C5 1.517(3) . ? C4 C6 1.541(3) . ? C4 H4A 1.0000 . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.503(3) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.315(3) . ? C7 H7A 0.9500 . ? C8 H8C 0.9500 . ? C8 H8A 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 C3 114.10(16) . . ? C1 N1 H1A 123.0 . . ? C3 N1 H1A 123.0 . . ? C1 O1 C2 109.70(15) . . ? C5 O3 H3A 109.5 . . ? O2 C1 N1 128.17(18) . . ? O2 C1 O1 121.71(18) . . ? N1 C1 O1 110.11(16) . . ? O1 C2 C3 105.94(13) . . ? O1 C2 H2A 110.5 . . ? C3 C2 H2A 110.5 . . ? O1 C2 H2B 110.5 . . ? C3 C2 H2B 110.5 . . ? H2A C2 H2B 108.7 . . ? N1 C3 C4 111.09(14) . . ? N1 C3 C2 100.00(14) . . ? C4 C3 C2 117.26(14) . . ? N1 C3 H3B 109.3 . . ? C4 C3 H3B 109.3 . . ? C2 C3 H3B 109.3 . . ? C5 C4 C3 111.41(14) . . ? C5 C4 C6 111.79(15) . . ? C3 C4 C6 113.46(16) . . ? C5 C4 H4A 106.6 . . ? C3 C4 H4A 106.6 . . ? C6 C4 H4A 106.6 . . ? O3 C5 C4 109.58(15) . . ? O3 C5 H5A 109.8 . . ? C4 C5 H5A 109.8 . . ? O3 C5 H5B 109.8 . . ? C4 C5 H5B 109.8 . . ? H5A C5 H5B 108.2 . . ? C7 C6 C4 111.88(16) . . ? C7 C6 H6A 109.2 . . ? C4 C6 H6A 109.2 . . ? C7 C6 H6B 109.2 . . ? C4 C6 H6B 109.2 . . ? H6A C6 H6B 107.9 . . ? C8 C7 C6 125.12(19) . . ? C8 C7 H7A 117.4 . . ? C6 C7 H7A 117.4 . . ? C7 C8 H8C 120.0 . . ? C7 C8 H8A 120.0 . . ? H8C C8 H8A 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 C3 N1 C1 O2 -177.77(18) . . . . ? C3 N1 C1 O1 3.6(2) . . . . ? C2 O1 C1 O2 177.36(17) . . . . ? C2 O1 C1 N1 -3.9(2) . . . . ? C1 O1 C2 C3 2.71(18) . . . . ? C1 N1 C3 C4 -126.21(18) . . . . ? C1 N1 C3 C2 -1.7(2) . . . . ? O1 C2 C3 N1 -0.64(17) . . . . ? O1 C2 C3 C4 119.48(16) . . . . ? N1 C3 C4 C5 -163.15(15) . . . . ? C2 C3 C4 C5 82.8(2) . . . . ? N1 C3 C4 C6 69.64(19) . . . . ? C2 C3 C4 C6 -44.5(2) . . . . ? C3 C4 C5 O3 -61.83(19) . . . . ? C6 C4 C5 O3 66.29(18) . . . . ? C5 C4 C6 C7 72.64(19) . . . . ? C3 C4 C6 C7 -160.34(15) . . . . ? C4 C6 C7 C8 -111.9(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A O3 0.88 2.09 2.835(2) 142.1 1_655 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.53 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.228 _refine_diff_density_min -0.146 _refine_diff_density_rms 0.036 # start Validation Reply Form _vrf_PUBL004_GLOBAL ; PROBLEM: The contact author's name and address are missing, RESPONSE: ... ; _vrf_PUBL005_GLOBAL ; PROBLEM: Flack test results are meaningless. RESPONSE: ... The compound was enantiomerically pure, although there is no heavy atom to achive a sensible Flack parameter. ; _vrf_PUBL006_GLOBAL ; PROBLEM: _publ_requested_journal is missing RESPONSE: ... ; _vrf_PUBL008_GLOBAL ; PROBLEM: _publ_section_title is missing. Title of paper. RESPONSE: ... ; _vrf_PUBL009_GLOBAL ; PROBLEM: _publ_author_name is missing. List of author(s) name(s). RESPONSE: ... ; _vrf_PUBL010_GLOBAL ; PROBLEM: _publ_author_address is missing. Author(s) address(es). RESPONSE: ... ; _vrf_PUBL012_GLOBAL ; PROBLEM: _publ_section_abstract is missing. RESPONSE: ... ; # end Validation Reply Form # Attachment 'oic11_0m.cif' data_oic11_0m _database_code_depnum_ccdc_archive 'CCDC 791949' #TrackingRef 'oic11_0m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H30 Br2 N2 O4' _chemical_formula_weight 642.38 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 9.5861(10) _cell_length_b 14.7570(15) _cell_length_c 19.402(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2744.7(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3021 _cell_measurement_theta_min 2.74 _cell_measurement_theta_max 22.69 _exptl_crystal_description needles _exptl_crystal_colour colourless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.555 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1304 _exptl_absorpt_coefficient_mu 2.992 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5100 _exptl_absorpt_correction_T_max 0.7745 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 100 _diffrn_reflns_number 29383 _diffrn_reflns_av_R_equivalents 0.1326 _diffrn_reflns_av_sigmaI/netI 0.0623 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 25.25 _reflns_number_total 2820 _reflns_number_gt 1416 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0787P)^2^+7.4605P] 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(10) _chemical_absolute_configuration unk _refine_ls_number_reflns 2820 _refine_ls_number_parameters 344 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1119 _refine_ls_R_factor_gt 0.0652 _refine_ls_wR_factor_ref 0.1826 _refine_ls_wR_factor_gt 0.1519 _refine_ls_goodness_of_fit_ref 1.142 _refine_ls_restrained_S_all 1.142 _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 0.7412(2) 0.97952(12) 0.78919(8) 0.0732(6) Uani 1 1 d . . . Br2 Br 0.9022(2) 0.74460(14) 0.14710(12) 0.0993(8) Uani 1 1 d . . . N1 N 0.3793(17) 0.7931(9) 0.3874(7) 0.069(4) Uani 1 1 d . . . N2 N 0.4240(16) 0.9561(8) 0.4696(6) 0.056(4) Uani 1 1 d . . . H2AA H 0.3615 0.9433 0.5063 0.068 Uiso 1 1 d R . . O1 O 0.4776(15) 0.6674(9) 0.4258(7) 0.093(4) Uani 1 1 d . . . O2 O 0.6504(13) 0.9489(7) 0.4379(6) 0.066(3) Uani 1 1 d . . . O3 O 0.2989(15) 0.9655(10) 0.1708(7) 0.108(5) Uani 1 1 d . . . O4 O 0.1574(15) 0.9396(8) 0.5106(6) 0.089(4) Uani 1 1 d . . . H4 H 0.1143 0.9021 0.5352 0.133 Uiso 1 1 calc R . . C1 C 0.680(2) 0.9633(11) 0.6948(8) 0.065(5) Uani 1 1 d . . . C2 C 0.5556(17) 0.9274(10) 0.6808(8) 0.056(4) Uani 1 1 d . . . H2 H 0.4969 0.9066 0.7169 0.067 Uiso 1 1 calc R . . C3 C 0.5132(18) 0.9207(10) 0.6125(8) 0.062(4) Uani 1 1 d . . . H3 H 0.4250 0.8952 0.6015 0.074 Uiso 1 1 calc R . . C4 C 0.6031(19) 0.9526(9) 0.5588(7) 0.051(4) Uani 1 1 d . . . C5 C 0.732(2) 0.9857(12) 0.5748(7) 0.068(4) Uani 1 1 d . . . H5 H 0.7939 1.0033 0.5389 0.081 Uiso 1 1 calc R . . C6 C 0.7739(19) 0.9940(11) 0.6441(8) 0.074(5) Uani 1 1 d . . . H6 H 0.8618 1.0191 0.6562 0.089 Uiso 1 1 calc R . . C7 C 0.562(2) 0.9505(10) 0.4825(8) 0.055(4) Uani 1 1 d . . . C8 C 0.3705(17) 0.9635(12) 0.3997(8) 0.061(4) Uani 1 1 d . . . H8 H 0.4188 1.0166 0.3784 0.073 Uiso 1 1 calc R . . C9 C 0.2146(19) 0.9845(12) 0.3974(8) 0.069(5) Uani 1 1 d . . . H9 H 0.2000 1.0492 0.4111 0.083 Uiso 1 1 calc R . . C10 C 0.119(2) 0.9263(12) 0.4383(10) 0.081(6) Uani 1 1 d . . . H10 H 0.0206 0.9472 0.4311 0.098 Uiso 1 1 calc R . . C11 C 0.129(2) 0.8223(12) 0.4217(10) 0.084(6) Uani 1 1 d . . . H11A H 0.0560 0.7905 0.4485 0.101 Uiso 1 1 calc R . . H11B H 0.1070 0.8136 0.3723 0.101 Uiso 1 1 calc R . . C12 C 0.266(2) 0.7775(10) 0.4361(9) 0.077(5) Uani 1 1 d . . . H12A H 0.2977 0.7977 0.4822 0.092 Uiso 1 1 calc R . . H12B H 0.2496 0.7114 0.4389 0.092 Uiso 1 1 calc R . . C13 C 0.3981(18) 0.8815(9) 0.3513(8) 0.061(4) Uani 1 1 d . . . H13 H 0.4951 0.8854 0.3326 0.073 Uiso 1 1 calc R . . C14 C 0.2908(17) 0.9006(11) 0.2918(8) 0.068(5) Uani 1 1 d . . . H14 H 0.2370 0.8443 0.2811 0.081 Uiso 1 1 calc R . . C15 C 0.1906(18) 0.9754(13) 0.3180(8) 0.074(5) Uani 1 1 d . . . H15A H 0.0926 0.9585 0.3084 0.089 Uiso 1 1 calc R . . H15B H 0.2107 1.0336 0.2947 0.089 Uiso 1 1 calc R . . C16 C 0.375(2) 0.9304(13) 0.2279(8) 0.080(6) Uani 1 1 d . . . H16A H 0.4425 0.9772 0.2427 0.096 Uiso 1 1 calc R . . H16B H 0.4294 0.8776 0.2117 0.096 Uiso 1 1 calc R . . C17 C 0.235(2) 0.8970(10) 0.1339(9) 0.082(5) Uani 1 1 d . . . H17A H 0.1744 0.9246 0.0984 0.098 Uiso 1 1 calc R . . H17B H 0.1746 0.8620 0.1656 0.098 Uiso 1 1 calc R . . C18 C 0.3340(17) 0.8323(11) 0.0989(8) 0.056(4) Uani 1 1 d . . . C19 C 0.3093(17) 0.7430(13) 0.1020(8) 0.067(5) Uani 1 1 d . . . H19 H 0.2334 0.7224 0.1293 0.080 Uiso 1 1 calc R . . C20 C 0.389(2) 0.6794(11) 0.0676(9) 0.069(5) Uani 1 1 d . . . H20 H 0.3639 0.6171 0.0695 0.082 Uiso 1 1 calc R . . C21 C 0.503(2) 0.7058(14) 0.0309(9) 0.074(5) Uani 1 1 d . . . H21 H 0.5611 0.6620 0.0096 0.088 Uiso 1 1 calc R . . C22 C 0.533(2) 0.7964(16) 0.0251(10) 0.089(6) Uani 1 1 d . . . H22 H 0.6091 0.8165 -0.0019 0.107 Uiso 1 1 calc R . . C23 C 0.447(2) 0.8591(11) 0.0603(9) 0.073(5) Uani 1 1 d . . . H23 H 0.4682 0.9219 0.0571 0.088 Uiso 1 1 calc R . . C24 C 0.479(2) 0.7309(13) 0.3817(9) 0.077(6) Uani 1 1 d . . . C25 C 0.5823(18) 0.7383(11) 0.3279(8) 0.065(4) Uani 1 1 d . . . C26 C 0.721(2) 0.7630(11) 0.3387(10) 0.081(5) Uani 1 1 d . . . H26 H 0.7493 0.7794 0.3839 0.097 Uiso 1 1 calc R . . C27 C 0.8171(18) 0.7644(12) 0.2872(12) 0.085(6) Uani 1 1 d . . . H27 H 0.9113 0.7802 0.2965 0.102 Uiso 1 1 calc R . . C28 C 0.7741(16) 0.7420(11) 0.2193(9) 0.070(4) Uani 1 1 d . . . C29 C 0.6406(18) 0.7169(12) 0.2079(10) 0.078(5) Uani 1 1 d . . . H29 H 0.6120 0.7006 0.1627 0.094 Uiso 1 1 calc R . . C30 C 0.546(2) 0.7146(11) 0.2606(9) 0.080(6) Uani 1 1 d . . . H30 H 0.4529 0.6964 0.2511 0.096 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 0.0876(12) 0.0856(12) 0.0464(8) 0.0015(9) -0.0070(10) 0.0085(11) Br2 0.0841(13) 0.0891(14) 0.1248(17) -0.0155(15) 0.0273(13) 0.0022(13) N1 0.092(11) 0.058(9) 0.057(8) -0.011(7) 0.006(8) -0.013(9) N2 0.104(12) 0.034(7) 0.032(7) -0.003(5) -0.004(7) -0.006(8) O1 0.117(11) 0.079(9) 0.083(9) 0.003(8) -0.001(8) 0.004(8) O2 0.091(8) 0.056(7) 0.050(6) -0.004(6) -0.005(7) 0.000(6) O3 0.127(11) 0.096(10) 0.099(10) -0.020(9) -0.027(9) 0.013(9) O4 0.120(11) 0.074(9) 0.073(8) -0.020(7) 0.023(8) -0.017(7) C1 0.087(12) 0.055(10) 0.054(10) 0.014(8) -0.010(9) 0.019(10) C2 0.069(11) 0.050(9) 0.049(9) 0.000(7) 0.011(9) -0.007(8) C3 0.060(10) 0.059(10) 0.066(11) 0.000(9) -0.015(9) -0.002(9) C4 0.078(11) 0.035(8) 0.038(8) 0.000(7) -0.006(8) 0.004(8) C5 0.078(12) 0.083(11) 0.042(8) 0.006(8) 0.003(10) -0.009(12) C6 0.075(11) 0.085(12) 0.063(10) 0.007(10) 0.005(10) -0.008(11) C7 0.078(13) 0.041(9) 0.045(9) 0.004(7) -0.008(10) 0.009(9) C8 0.066(11) 0.053(10) 0.063(11) -0.008(9) -0.005(9) 0.000(9) C9 0.103(16) 0.054(10) 0.050(9) -0.026(8) -0.008(10) -0.005(11) C10 0.106(15) 0.064(12) 0.074(13) -0.044(11) 0.001(12) 0.004(12) C11 0.095(15) 0.085(13) 0.073(13) -0.007(11) 0.014(12) -0.027(12) C12 0.096(14) 0.046(10) 0.089(12) -0.004(8) -0.002(13) -0.009(11) C13 0.077(10) 0.056(10) 0.050(9) -0.006(8) -0.009(9) 0.005(9) C14 0.080(12) 0.063(10) 0.060(9) -0.012(9) -0.001(10) -0.010(9) C15 0.069(10) 0.079(12) 0.074(11) -0.011(10) -0.019(9) 0.004(10) C16 0.100(14) 0.084(12) 0.055(11) -0.015(9) -0.029(10) 0.021(12) C17 0.082(12) 0.062(10) 0.102(13) -0.031(10) -0.033(13) 0.001(11) C18 0.062(10) 0.049(10) 0.056(10) -0.022(8) -0.002(9) -0.005(9) C19 0.062(10) 0.085(14) 0.054(10) -0.018(10) -0.006(8) -0.001(11) C20 0.078(12) 0.055(10) 0.073(11) -0.019(10) -0.014(11) -0.005(11) C21 0.099(15) 0.072(14) 0.049(11) 0.007(10) 0.001(11) 0.011(12) C22 0.091(14) 0.105(17) 0.072(13) 0.035(12) 0.018(11) 0.009(14) C23 0.089(14) 0.051(10) 0.080(13) 0.012(10) -0.008(12) 0.002(10) C24 0.116(16) 0.063(13) 0.051(10) -0.006(10) -0.019(11) 0.035(13) C25 0.077(12) 0.057(10) 0.061(11) -0.020(9) -0.016(10) 0.021(10) C26 0.092(14) 0.059(11) 0.091(13) -0.011(10) -0.037(12) 0.007(11) C27 0.055(10) 0.074(13) 0.125(16) -0.034(14) 0.004(12) 0.001(10) C28 0.058(11) 0.063(10) 0.088(12) -0.003(10) -0.020(10) 0.013(9) C29 0.074(12) 0.091(13) 0.070(11) -0.025(11) -0.010(11) 0.029(10) C30 0.096(16) 0.069(12) 0.076(12) -0.021(10) -0.006(12) 0.019(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C1 1.938(16) . ? Br2 C28 1.863(17) . ? N1 C24 1.33(2) . ? N1 C12 1.46(2) . ? N1 C13 1.491(19) . ? N2 C7 1.35(2) . ? N2 C8 1.454(19) . ? N2 H2AA 0.9499 . ? O1 C24 1.27(2) . ? O2 C7 1.208(18) . ? O3 C17 1.381(19) . ? O3 C16 1.424(19) . ? O4 C10 1.46(2) . ? O4 H4 0.8400 . ? C1 C2 1.33(2) . ? C1 C6 1.41(2) . ? C2 C3 1.39(2) . ? C2 H2 0.9500 . ? C3 C4 1.43(2) . ? C3 H3 0.9500 . ? C4 C5 1.36(2) . ? C4 C7 1.53(2) . ? C5 C6 1.41(2) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C8 C9 1.53(2) . ? C8 C13 1.56(2) . ? C8 H8 1.0000 . ? C9 C10 1.49(2) . ? C9 C15 1.56(2) . ? C9 H9 1.0000 . ? C10 C11 1.57(2) . ? C10 H10 1.0000 . ? C11 C12 1.50(3) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.57(2) . ? C13 H13 1.0000 . ? C14 C15 1.55(2) . ? C14 C16 1.54(2) . ? C14 H14 1.0000 . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.51(2) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.34(2) . ? C18 C23 1.38(2) . ? C19 C20 1.38(2) . ? C19 H19 0.9500 . ? C20 C21 1.36(2) . ? C20 H20 0.9500 . ? C21 C22 1.37(3) . ? C21 H21 0.9500 . ? C22 C23 1.41(2) . ? C22 H22 0.9500 . ? C23 H23 0.9500 . ? C24 C25 1.44(2) . ? C25 C26 1.39(2) . ? C25 C30 1.40(2) . ? C26 C27 1.36(2) . ? C26 H26 0.9500 . ? C27 C28 1.42(2) . ? C27 H27 0.9500 . ? C28 C29 1.35(2) . ? C29 C30 1.37(2) . ? C29 H29 0.9500 . ? C30 H30 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 C24 N1 C12 118.7(15) . . ? C24 N1 C13 118.5(16) . . ? C12 N1 C13 122.1(14) . . ? C7 N2 C8 121.5(13) . . ? C7 N2 H2AA 117.9 . . ? C8 N2 H2AA 119.5 . . ? C17 O3 C16 111.3(14) . . ? C10 O4 H4 109.5 . . ? C2 C1 C6 123.9(16) . . ? C2 C1 Br1 120.9(13) . . ? C6 C1 Br1 115.2(13) . . ? C1 C2 C3 119.0(15) . . ? C1 C2 H2 120.5 . . ? C3 C2 H2 120.5 . . ? C2 C3 C4 119.6(15) . . ? C2 C3 H3 120.2 . . ? C4 C3 H3 120.2 . . ? C5 C4 C3 119.8(13) . . ? C5 C4 C7 117.3(14) . . ? C3 C4 C7 122.9(15) . . ? C4 C5 C6 120.4(15) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? C5 C6 C1 117.1(16) . . ? C5 C6 H6 121.4 . . ? C1 C6 H6 121.4 . . ? O2 C7 N2 123.6(14) . . ? O2 C7 C4 120.9(16) . . ? N2 C7 C4 115.3(15) . . ? N2 C8 C9 112.8(14) . . ? N2 C8 C13 116.4(14) . . ? C9 C8 C13 107.9(13) . . ? N2 C8 H8 106.4 . . ? C9 C8 H8 106.4 . . ? C13 C8 H8 106.4 . . ? C10 C9 C8 118.1(17) . . ? C10 C9 C15 112.6(15) . . ? C8 C9 C15 98.9(14) . . ? C10 C9 H9 108.8 . . ? C8 C9 H9 108.8 . . ? C15 C9 H9 108.8 . . ? O4 C10 C9 106.1(14) . . ? O4 C10 C11 108.1(16) . . ? C9 C10 C11 114.6(16) . . ? O4 C10 H10 109.3 . . ? C9 C10 H10 109.3 . . ? C11 C10 H10 109.3 . . ? C12 C11 C10 116.6(16) . . ? C12 C11 H11A 108.2 . . ? C10 C11 H11A 108.2 . . ? C12 C11 H11B 108.2 . . ? C10 C11 H11B 108.2 . . ? H11A C11 H11B 107.3 . . ? N1 C12 C11 117.5(14) . . ? N1 C12 H12A 107.9 . . ? C11 C12 H12A 107.9 . . ? N1 C12 H12B 107.9 . . ? C11 C12 H12B 107.9 . . ? H12A C12 H12B 107.2 . . ? N1 C13 C8 112.1(13) . . ? N1 C13 C14 115.0(13) . . ? C8 C13 C14 101.1(12) . . ? N1 C13 H13 109.4 . . ? C8 C13 H13 109.4 . . ? C14 C13 H13 109.4 . . ? C15 C14 C16 112.6(14) . . ? C15 C14 C13 107.0(13) . . ? C16 C14 C13 107.4(13) . . ? C15 C14 H14 109.9 . . ? C16 C14 H14 109.9 . . ? C13 C14 H14 109.9 . . ? C14 C15 C9 107.1(14) . . ? C14 C15 H15A 110.3 . . ? C9 C15 H15A 110.3 . . ? C14 C15 H15B 110.3 . . ? C9 C15 H15B 110.3 . . ? H15A C15 H15B 108.6 . . ? O3 C16 C14 117.5(15) . . ? O3 C16 H16A 107.9 . . ? C14 C16 H16A 107.9 . . ? O3 C16 H16B 107.9 . . ? C14 C16 H16B 107.9 . . ? H16A C16 H16B 107.2 . . ? O3 C17 C18 114.8(15) . . ? O3 C17 H17A 108.6 . . ? C18 C17 H17A 108.6 . . ? O3 C17 H17B 108.6 . . ? C18 C17 H17B 108.6 . . ? H17A C17 H17B 107.6 . . ? C19 C18 C23 116.5(15) . . ? C19 C18 C17 119.5(16) . . ? C23 C18 C17 123.9(16) . . ? C18 C19 C20 123.3(17) . . ? C18 C19 H19 118.3 . . ? C20 C19 H19 118.3 . . ? C21 C20 C19 120.0(17) . . ? C21 C20 H20 120.0 . . ? C19 C20 H20 120.0 . . ? C20 C21 C22 119.4(19) . . ? C20 C21 H21 120.3 . . ? C22 C21 H21 120.3 . . ? C21 C22 C23 119(2) . . ? C21 C22 H22 120.7 . . ? C23 C22 H22 120.7 . . ? C18 C23 C22 122.1(16) . . ? C18 C23 H23 118.9 . . ? C22 C23 H23 118.9 . . ? O1 C24 N1 116.4(19) . . ? O1 C24 C25 123.6(17) . . ? N1 C24 C25 120.0(17) . . ? C26 C25 C30 116.3(18) . . ? C26 C25 C24 124.4(15) . . ? C30 C25 C24 119.2(17) . . ? C27 C26 C25 122.8(16) . . ? C27 C26 H26 118.6 . . ? C25 C26 H26 118.6 . . ? C26 C27 C28 118.7(15) . . ? C26 C27 H27 120.6 . . ? C28 C27 H27 120.6 . . ? C29 C28 C27 119.4(17) . . ? C29 C28 Br2 120.5(15) . . ? C27 C28 Br2 120.1(13) . . ? C28 C29 C30 120.9(18) . . ? C28 C29 H29 119.5 . . ? C30 C29 H29 119.5 . . ? C29 C30 C25 121.9(19) . . ? C29 C30 H30 119.1 . . ? C25 C30 H30 119.1 . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 22.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.799 _refine_diff_density_min -0.583 _refine_diff_density_rms 0.097 # start Validation Reply Form _vrf_PUBL004_GLOBAL ; PROBLEM: The contact author's name and address are missing, RESPONSE: ... ; _vrf_PUBL005_GLOBAL ; PROBLEM: _publ_contact_author_email, _publ_contact_author_fax and RESPONSE: ... ; _vrf_PUBL006_GLOBAL ; PROBLEM: _publ_requested_journal is missing RESPONSE: ... ; _vrf_PUBL008_GLOBAL ; PROBLEM: _publ_section_title is missing. Title of paper. RESPONSE: ... ; _vrf_PUBL009_GLOBAL ; PROBLEM: _publ_author_name is missing. List of author(s) name(s). RESPONSE: ... ; _vrf_PUBL010_GLOBAL ; PROBLEM: _publ_author_address is missing. Author(s) address(es). RESPONSE: ... ; _vrf_PUBL012_GLOBAL ; PROBLEM: _publ_section_abstract is missing. RESPONSE: ... ; _vrf_PLAT027_oic11_0m ; PROBLEM: _diffrn_reflns_theta_full (too) Low ............ 22.50 Deg. RESPONSE: ... The crystal was a poor diffractor.. During data collection the crystal decomposed. Attempts to find another crystal proved unsucessful. The overall structure is clearly visible. ; _vrf_PLAT035_oic11_0m ; PROBLEM: No _chemical_absolute_configuration info given . ? RESPONSE: ... This problem is corrected ; # end Validation Reply Form