# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 loop_ _publ_author_name S.Ley 'Henriette M. Hansen' 'Deborah A. Longbottom' _publ_contact_author_name S.Ley _publ_contact_author_address ; Department of Chemistry University of Cambridge Lensfield Road Cambridge CB2 1EW UNITED KINGDOM ; _publ_contact_author_email SVL1000@CAM.AC.UK _publ_requested_journal 'Chemical Communications' _publ_section_title ; A new asymmetric organocatalytic nitrocyclopropanation reaction ; _ccdc_publ_extra_info 'bccab file in email and history' data_sl0635 _database_code_depnum_ccdc_archive 'CCDC 618771' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7 H9 N O3' _chemical_formula_sum 'C7 H9 N O3' _chemical_formula_weight 155.15 _chemical_absolute_configuration ; Absolute structure unknown! 666 Friedel pairs averaged for the refinement. ; 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' _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+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 5.4987(3) _cell_length_b 9.8391(5) _cell_length_c 13.5025(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 730.52(6) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 5151 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.411 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 328 _exptl_absorpt_coefficient_mu 0.111 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.819 _exptl_absorpt_correction_T_max 1.002 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; No unusual features. ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 5667 _diffrn_reflns_av_R_equivalents 0.0677 _diffrn_reflns_av_sigmaI/netI 0.0552 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.66 _diffrn_reflns_theta_max 27.47 _reflns_number_total 997 _reflns_number_gt 819 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _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^)+(0.0323P)^2^+0.2405P] 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 3(2) _refine_ls_number_reflns 997 _refine_ls_number_parameters 100 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0614 _refine_ls_R_factor_gt 0.0437 _refine_ls_wR_factor_ref 0.0879 _refine_ls_wR_factor_gt 0.0808 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _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 O1 O -0.1114(3) -0.19185(17) 0.46677(12) 0.0286(4) Uani 1 1 d . . . O2 O 0.3200(3) 0.21187(18) 0.56594(12) 0.0322(5) Uani 1 1 d . . . O3 O 0.6258(4) 0.08914(18) 0.61385(12) 0.0343(5) Uani 1 1 d . . . N1 N 0.4527(4) 0.1122(2) 0.55856(15) 0.0269(5) Uani 1 1 d . . . C1 C 0.0567(5) -0.1415(2) 0.42073(17) 0.0237(6) Uani 1 1 d . . . C2 C 0.1446(4) -0.0033(2) 0.44748(16) 0.0230(5) Uani 1 1 d . . . H2 H 0.0247 0.0561 0.4825 0.028 Uiso 1 1 calc R . . C3 C 0.3246(5) 0.0693(2) 0.38143(16) 0.0260(6) Uani 1 1 d . . . H3 H 0.3080 0.1704 0.3774 0.031 Uiso 1 1 calc R . . C4 C 0.4119(5) -0.0019(3) 0.28832(16) 0.0295(6) Uani 1 1 d . . . H4A H 0.5792 0.0288 0.2731 0.035 Uiso 1 1 calc R . . H4B H 0.3061 0.0248 0.2322 0.035 Uiso 1 1 calc R . . C5 C 0.4107(5) -0.1563(2) 0.29783(17) 0.0269(6) Uani 1 1 d . . . H5A H 0.5354 -0.1843 0.3466 0.032 Uiso 1 1 calc R . . H5B H 0.4538 -0.1972 0.2332 0.032 Uiso 1 1 calc R . . C6 C 0.1626(5) -0.2100(3) 0.33068(17) 0.0273(6) Uani 1 1 d . . . H6A H 0.0469 -0.1996 0.2750 0.033 Uiso 1 1 calc R . . H6B H 0.1780 -0.3085 0.3446 0.033 Uiso 1 1 calc R . . C7 C 0.4079(5) 0.0130(3) 0.47903(15) 0.0235(5) Uani 1 1 d . . . H7 H 0.5130 -0.0699 0.4775 0.028 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 O1 0.0203(9) 0.0266(10) 0.0389(9) 0.0058(7) 0.0024(8) -0.0020(8) O2 0.0358(11) 0.0241(9) 0.0366(9) -0.0054(8) 0.0054(8) 0.0016(9) O3 0.0365(11) 0.0342(10) 0.0321(9) -0.0039(8) -0.0079(9) -0.0012(9) N1 0.0300(13) 0.0235(11) 0.0271(10) 0.0006(9) 0.0030(10) -0.0038(10) C1 0.0173(12) 0.0264(13) 0.0275(13) 0.0045(10) -0.0052(10) 0.0032(11) C2 0.0224(12) 0.0202(11) 0.0265(11) 0.0012(9) 0.0028(10) 0.0026(11) C3 0.0290(14) 0.0224(13) 0.0268(12) 0.0017(10) 0.0029(11) 0.0002(11) C4 0.0355(16) 0.0262(13) 0.0269(12) 0.0003(10) 0.0062(11) -0.0051(14) C5 0.0294(14) 0.0255(13) 0.0260(12) -0.0057(10) 0.0040(11) 0.0021(12) C6 0.0321(15) 0.0230(13) 0.0269(11) -0.0012(10) -0.0028(11) -0.0006(13) C7 0.0242(13) 0.0202(12) 0.0260(11) -0.0021(9) 0.0019(10) -0.0016(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 O1 C1 1.219(3) . ? O2 N1 1.226(3) . ? O3 N1 1.231(3) . ? N1 C7 1.472(3) . ? C1 C2 1.487(3) . ? C1 C6 1.508(3) . ? C2 C3 1.512(3) . ? C2 C7 1.517(3) . ? C2 H2 1.0000 . ? C3 C7 1.501(3) . ? C3 C4 1.517(3) . ? C3 H3 1.0000 . ? C4 C5 1.525(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.528(4) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 H7 1.0000 . ? 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 O2 N1 O3 123.9(2) . . ? O2 N1 C7 119.3(2) . . ? O3 N1 C7 116.7(2) . . ? O1 C1 C2 119.6(2) . . ? O1 C1 C6 121.5(2) . . ? C2 C1 C6 118.6(2) . . ? C1 C2 C3 120.1(2) . . ? C1 C2 C7 118.3(2) . . ? C3 C2 C7 59.42(15) . . ? C1 C2 H2 115.8 . . ? C3 C2 H2 115.8 . . ? C7 C2 H2 115.8 . . ? C7 C3 C2 60.48(15) . . ? C7 C3 C4 117.4(2) . . ? C2 C3 C4 118.5(2) . . ? C7 C3 H3 116.3 . . ? C2 C3 H3 116.3 . . ? C4 C3 H3 116.3 . . ? C3 C4 C5 112.89(19) . . ? C3 C4 H4A 109.0 . . ? C5 C4 H4A 109.0 . . ? C3 C4 H4B 109.0 . . ? C5 C4 H4B 109.0 . . ? H4A C4 H4B 107.8 . . ? C4 C5 C6 111.9(2) . . ? C4 C5 H5A 109.2 . . ? C6 C5 H5A 109.2 . . ? C4 C5 H5B 109.2 . . ? C6 C5 H5B 109.2 . . ? H5A C5 H5B 107.9 . . ? C1 C6 C5 115.1(2) . . ? C1 C6 H6A 108.5 . . ? C5 C6 H6A 108.5 . . ? C1 C6 H6B 108.5 . . ? C5 C6 H6B 108.5 . . ? H6A C6 H6B 107.5 . . ? N1 C7 C3 116.5(2) . . ? N1 C7 C2 115.8(2) . . ? C3 C7 C2 60.10(16) . . ? N1 C7 H7 117.3 . . ? C3 C7 H7 117.3 . . ? C2 C7 H7 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 O1 C1 C2 C3 -170.3(2) . . . . ? C6 C1 C2 C3 3.8(3) . . . . ? O1 C1 C2 C7 120.5(2) . . . . ? C6 C1 C2 C7 -65.3(3) . . . . ? C1 C2 C3 C7 -107.1(2) . . . . ? C1 C2 C3 C4 0.0(3) . . . . ? C7 C2 C3 C4 107.1(2) . . . . ? C7 C3 C4 C5 40.8(3) . . . . ? C2 C3 C4 C5 -28.8(3) . . . . ? C3 C4 C5 C6 53.5(3) . . . . ? O1 C1 C6 C5 -164.3(2) . . . . ? C2 C1 C6 C5 21.6(3) . . . . ? C4 C5 C6 C1 -50.5(3) . . . . ? O2 N1 C7 C3 36.8(3) . . . . ? O3 N1 C7 C3 -142.7(2) . . . . ? O2 N1 C7 C2 -31.0(3) . . . . ? O3 N1 C7 C2 149.5(2) . . . . ? C2 C3 C7 N1 -105.9(2) . . . . ? C4 C3 C7 N1 145.2(2) . . . . ? C4 C3 C7 C2 -108.9(2) . . . . ? C1 C2 C7 N1 -142.8(2) . . . . ? C3 C2 C7 N1 107.1(2) . . . . ? C1 C2 C7 C3 110.1(2) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.193 _refine_diff_density_min -0.255 _refine_diff_density_rms 0.064