# Electronic Supplementary Material (ESI) for Green Chemistry # 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_sl1305 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H6 Cl N O2' _chemical_formula_sum 'C8 H6 Cl N O2' _chemical_formula_weight 183.59 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' Cl Cl 0.1484 0.1585 '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)/n _symmetry_space_group_name_Hall '-P 2yn' 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 7.3073(3) _cell_length_b 7.1368(3) _cell_length_c 15.6263(7) _cell_angle_alpha 90.00 _cell_angle_beta 91.452(2) _cell_angle_gamma 90.00 _cell_volume 814.66(6) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 4702 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 30.03 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.497 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 376 _exptl_absorpt_coefficient_mu 0.421 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.772 _exptl_absorpt_correction_T_max 0.931 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(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 5569 _diffrn_reflns_av_R_equivalents 0.0328 _diffrn_reflns_av_sigmaI/netI 0.0352 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.99 _diffrn_reflns_theta_max 30.03 _reflns_number_total 2309 _reflns_number_gt 1917 _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^)+(0.0831P)^2^+0.3534P] 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 2309 _refine_ls_number_parameters 109 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0625 _refine_ls_R_factor_gt 0.0541 _refine_ls_wR_factor_ref 0.1594 _refine_ls_wR_factor_gt 0.1546 _refine_ls_goodness_of_fit_ref 1.085 _refine_ls_restrained_S_all 1.085 _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 Cl1 Cl 0.57167(7) 0.04497(8) 0.66361(3) 0.0472(2) Uani 1 1 d . . . C1 C 0.6495(2) 0.2343(3) 0.60364(11) 0.0347(4) Uani 1 1 d . . . C2 C 0.6875(3) 0.4016(3) 0.64380(12) 0.0403(4) Uani 1 1 d . . . H2 H 0.6726 0.4147 0.7037 0.048 Uiso 1 1 calc R . . C3 C 0.7477(3) 0.5502(3) 0.59554(13) 0.0403(4) Uani 1 1 d . . . H3 H 0.7760 0.6659 0.6229 0.048 Uiso 1 1 calc R . . C4 C 0.7677(2) 0.5340(3) 0.50726(12) 0.0346(4) Uani 1 1 d . . . C5 C 0.7285(3) 0.3604(3) 0.46814(11) 0.0365(4) Uani 1 1 d . . . H5 H 0.7419 0.3464 0.4082 0.044 Uiso 1 1 calc R . . C6 C 0.6707(2) 0.2100(3) 0.51635(11) 0.0366(4) Uani 1 1 d . . . H6 H 0.6459 0.0923 0.4902 0.044 Uiso 1 1 calc R . . C7 C 0.8305(2) 0.6971(3) 0.45918(13) 0.0380(4) Uani 1 1 d . . . H7 H 0.8720 0.8033 0.4907 0.046 Uiso 1 1 calc R . . C8 C 0.8330(3) 0.7060(3) 0.37497(13) 0.0428(4) Uani 1 1 d . . . H8 H 0.7916 0.6023 0.3416 0.051 Uiso 1 1 calc R . . N1 N 0.8993(2) 0.8750(3) 0.33261(12) 0.0456(4) Uani 1 1 d . . . O1 O 0.8948(3) 0.8656(3) 0.25381(11) 0.0652(5) Uani 1 1 d . . . O2 O 0.9513(3) 1.0099(3) 0.37322(13) 0.0580(4) 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 Cl1 0.0452(3) 0.0534(3) 0.0430(3) 0.0167(2) 0.0001(2) 0.0019(2) C1 0.0289(8) 0.0427(9) 0.0323(8) 0.0063(7) -0.0015(6) 0.0043(7) C2 0.0405(9) 0.0481(11) 0.0322(8) -0.0040(8) -0.0001(7) 0.0093(8) C3 0.0408(10) 0.0379(10) 0.0420(10) -0.0068(7) -0.0021(7) 0.0073(8) C4 0.0284(8) 0.0360(9) 0.0392(9) 0.0039(7) -0.0007(6) 0.0057(7) C5 0.0388(9) 0.0410(10) 0.0297(8) 0.0011(7) 0.0009(7) 0.0025(7) C6 0.0392(9) 0.0366(9) 0.0337(8) -0.0005(7) -0.0028(7) -0.0005(7) C7 0.0339(9) 0.0377(9) 0.0424(9) 0.0025(7) -0.0001(7) 0.0058(7) C8 0.0403(10) 0.0439(11) 0.0444(10) 0.0046(8) 0.0023(8) 0.0017(8) N1 0.0387(8) 0.0503(10) 0.0482(9) 0.0124(8) 0.0089(7) 0.0065(8) O1 0.0792(12) 0.0701(12) 0.0469(9) 0.0140(8) 0.0118(8) -0.0079(10) O2 0.0609(10) 0.0452(9) 0.0682(11) 0.0029(8) 0.0063(8) 0.0015(8) _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 Cl1 C1 1.748(2) . ? C1 C2 1.374(3) . ? C1 C6 1.388(2) . ? C2 C3 1.380(3) . ? C2 H2 0.9500 . ? C3 C4 1.396(3) . ? C3 H3 0.9500 . ? C4 C5 1.407(3) . ? C4 C7 1.465(3) . ? C5 C6 1.384(3) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C8 1.318(3) . ? C7 H7 0.9500 . ? C8 N1 1.465(3) . ? C8 H8 0.9500 . ? N1 O2 1.209(3) . ? N1 O1 1.233(2) . ? 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 C2 C1 C6 122.10(18) . . ? C2 C1 Cl1 119.46(14) . . ? C6 C1 Cl1 118.44(15) . . ? C1 C2 C3 118.82(17) . . ? C1 C2 H2 120.6 . . ? C3 C2 H2 120.6 . . ? C2 C3 C4 121.26(18) . . ? C2 C3 H3 119.4 . . ? C4 C3 H3 119.4 . . ? C3 C4 C5 118.50(17) . . ? C3 C4 C7 118.87(18) . . ? C5 C4 C7 122.63(17) . . ? C6 C5 C4 120.52(16) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C5 C6 C1 118.78(18) . . ? C5 C6 H6 120.6 . . ? C1 C6 H6 120.6 . . ? C8 C7 C4 124.2(2) . . ? C8 C7 H7 117.9 . . ? C4 C7 H7 117.9 . . ? C7 C8 N1 120.3(2) . . ? C7 C8 H8 119.9 . . ? N1 C8 H8 119.9 . . ? O2 N1 O1 124.6(2) . . ? O2 N1 C8 121.47(19) . . ? O1 N1 C8 113.9(2) . . ? _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 30.03 _diffrn_measured_fraction_theta_full 0.969 _refine_diff_density_max 0.968 _refine_diff_density_min -0.617 _refine_diff_density_rms 0.061 _database_code_depnum_ccdc_archive 'CCDC 940593'