# 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_lyh #TrackingRef '6-Cl.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H6 Cl N O2' _chemical_formula_sum 'C9 H6 Cl N O2' _chemical_formula_weight 195.60 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' Cl Cl 0.1484 0.1585 '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 triclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall '-P 2ybc' 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 7.2608(15) _cell_length_b 11.973(2) _cell_length_c 9.6567(19) _cell_angle_alpha 90.00 _cell_angle_beta 98.88(3) _cell_angle_gamma 90.00 _cell_volume 829.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 494 _cell_measurement_theta_min 3.31 _cell_measurement_theta_max 17.22 _exptl_crystal_description Prism _exptl_crystal_colour White _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.566 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 400 _exptl_absorpt_coefficient_mu 0.419 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9200 _exptl_absorpt_correction_T_max 0.9200 _exptl_absorpt_process_details 'CrystalClear (Rigaku, 2005)' _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 'Rigaku SCXmini diffractometer' _diffrn_measurement_method CCD_Profile_fitting _diffrn_detector_area_resol_mean 13.6612 _diffrn_standards_number ? _diffrn_standards_interval_count 2 _diffrn_standards_interval_time 150 _diffrn_standards_decay_% 0 _diffrn_reflns_number 2525 _diffrn_reflns_av_R_equivalents 0.1469 _diffrn_reflns_av_sigmaI/netI 0.0904 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 3.31 _diffrn_reflns_theta_max 17.22 _reflns_number_total 494 _reflns_number_gt 461 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku, 2005)' _computing_cell_refinement 'CrystalClear (Rigaku, 2005)' _computing_data_reduction 'CrystalClear (Rigaku, 2005)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'DIAMOND (Brandenburg & Putz, 2005)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.1313P)^2^+44.4177P] 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 494 _refine_ls_number_parameters 131 _refine_ls_number_restraints 78 _refine_ls_R_factor_all 0.1783 _refine_ls_R_factor_gt 0.1691 _refine_ls_wR_factor_ref 0.3962 _refine_ls_wR_factor_gt 0.3918 _refine_ls_goodness_of_fit_ref 1.187 _refine_ls_restrained_S_all 1.094 _refine_ls_shift/su_max 0.346 _refine_ls_shift/su_mean 0.003 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 0.011(4) 0.873(3) 0.626(3) 0.024(7) Uani 0.50 1 d PU . . O2 O 0.396(2) 0.9337(13) 1.3384(16) 0.039(5) Uani 1 1 d U . . H2 H 0.4359 0.9232 1.4216 0.058 Uiso 1 1 calc R . . N1 N 0.320(3) 1.176(2) 0.972(2) 0.036(7) Uani 1 1 d U . . C10 C 0.382(3) 1.173(2) 1.110(2) 0.031(7) Uani 1 1 d U . . H10 H 0.4357 1.2330 1.1611 0.037 Uiso 1 1 calc R . . C11 C 0.355(3) 1.069(2) 1.166(3) 0.030(7) Uani 1 1 d U . . C12 C 0.413(3) 1.042(2) 1.308(3) 0.039(8) Uani 1 1 d U . . C13 C 0.276(3) 1.001(2) 1.047(3) 0.033(7) Uani 1 1 d U . . C14 C 0.249(3) 1.074(2) 0.929(3) 0.035(7) Uani 1 1 d U . . C15 C 0.175(3) 1.038(2) 0.798(3) 0.036(8) Uani 1 1 d U . . H15 H 0.1578 1.0859 0.7213 0.043 Uiso 1 1 calc R . . C16 C 0.129(3) 0.928(2) 0.786(2) 0.027(7) Uani 1 1 d U . . C17 C 0.149(3) 0.854(2) 0.898(2) 0.025(7) Uani 1 1 d U . . H17 H 0.1133 0.7794 0.8829 0.030 Uiso 1 1 calc R . . C18 C 0.221(3) 0.888(2) 1.029(3) 0.035(7) Uani 1 1 d U . . H18 H 0.2334 0.8392 1.1046 0.041 Uiso 1 1 calc R . . Cl1' Cl 0.058(4) 0.882(3) 0.610(4) 0.063(14) Uani 0.50 1 d PU . . O1' O 0.424(6) 1.112(3) 1.397(3) 0.010(11) Uiso 0.50 1 d P . . O3 O 0.508(5) 1.113(2) 1.400(3) 0.004(11) Uiso 0.50 1 d P . . H1 H 0.31(2) 1.238(15) 0.917(17) 0.00(5) 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 Cl1 0.024(11) 0.027(10) 0.023(10) -0.012(7) 0.010(8) -0.004(7) O2 0.047(9) 0.029(9) 0.039(9) 0.004(7) 0.005(7) -0.003(7) N1 0.037(10) 0.035(10) 0.034(10) 0.004(9) 0.000(8) -0.011(8) C10 0.042(11) 0.025(11) 0.026(11) -0.004(9) 0.006(9) 0.002(8) C11 0.032(10) 0.028(10) 0.030(11) 0.004(9) 0.002(8) 0.009(8) C12 0.042(11) 0.037(11) 0.041(11) 0.002(9) 0.011(9) -0.001(9) C13 0.031(10) 0.032(11) 0.039(11) -0.001(9) 0.012(8) 0.004(8) C14 0.038(11) 0.032(11) 0.035(11) -0.002(9) 0.004(9) -0.003(9) C15 0.037(11) 0.032(11) 0.040(11) 0.005(9) 0.005(9) 0.006(8) C16 0.031(10) 0.025(10) 0.026(10) -0.008(9) 0.005(8) -0.005(8) C17 0.026(10) 0.024(10) 0.026(10) 0.001(9) 0.006(8) -0.003(8) C18 0.036(11) 0.032(11) 0.035(11) 0.007(8) 0.005(8) -0.011(8) Cl1' 0.065(17) 0.061(16) 0.063(16) -0.005(8) 0.009(9) -0.005(9) _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 C16 1.77(4) . ? O2 C12 1.34(3) . ? O2 H2 0.8200 . ? N1 C10 1.34(3) . ? N1 C14 1.37(3) . ? N1 H1 0.91(18) . ? C10 C11 1.38(3) . ? C10 H10 0.9300 . ? C11 C12 1.40(3) . ? C11 C13 1.45(3) . ? C12 O1' 1.19(3) . ? C12 O3 1.34(4) . ? C13 C18 1.41(3) . ? C13 C14 1.42(3) . ? C14 C15 1.37(3) . ? C15 C16 1.36(3) . ? C15 H15 0.9300 . ? C16 C17 1.39(3) . ? C16 Cl1' 1.78(4) . ? C17 C18 1.36(3) . ? C17 H17 0.9300 . ? C18 H18 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 C12 O2 H2 109.5 . . ? C10 N1 C14 109(2) . . ? C10 N1 H1 126(10) . . ? C14 N1 H1 123(10) . . ? N1 C10 C11 112(2) . . ? N1 C10 H10 124.0 . . ? C11 C10 H10 124.0 . . ? C10 C11 C12 124(2) . . ? C10 C11 C13 104(2) . . ? C12 C11 C13 132(2) . . ? O1' C12 O2 121(3) . . ? O1' C12 O3 26.8(19) . . ? O2 C12 O3 122(2) . . ? O1' C12 C11 121(3) . . ? O2 C12 C11 114(2) . . ? O3 C12 C11 123(2) . . ? C18 C13 C14 119(2) . . ? C18 C13 C11 134(2) . . ? C14 C13 C11 106(2) . . ? C15 C14 N1 130(2) . . ? C15 C14 C13 122(2) . . ? N1 C14 C13 108(2) . . ? C16 C15 C14 116(2) . . ? C16 C15 H15 121.9 . . ? C14 C15 H15 121.9 . . ? C15 C16 C17 124(2) . . ? C15 C16 Cl1 121(2) . . ? C17 C16 Cl1 115(2) . . ? C15 C16 Cl1' 114(2) . . ? C17 C16 Cl1' 122(2) . . ? Cl1 C16 Cl1' 13.3(17) . . ? C18 C17 C16 121(2) . . ? C18 C17 H17 119.7 . . ? C16 C17 H17 119.7 . . ? C17 C18 C13 118(2) . . ? C17 C18 H18 121.1 . . ? C13 C18 H18 121.1 . . ? 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 C14 N1 C10 C11 0(3) . . . . ? N1 C10 C11 C12 178(2) . . . . ? N1 C10 C11 C13 3(3) . . . . ? C10 C11 C12 O1' 28(4) . . . . ? C13 C11 C12 O1' -158(3) . . . . ? C10 C11 C12 O2 -172(2) . . . . ? C13 C11 C12 O2 2(4) . . . . ? C10 C11 C12 O3 -4(4) . . . . ? C13 C11 C12 O3 170(3) . . . . ? C10 C11 C13 C18 178(2) . . . . ? C12 C11 C13 C18 3(4) . . . . ? C10 C11 C13 C14 -4(2) . . . . ? C12 C11 C13 C14 -179(2) . . . . ? C10 N1 C14 C15 -178(2) . . . . ? C10 N1 C14 C13 -3(3) . . . . ? C18 C13 C14 C15 -1(3) . . . . ? C11 C13 C14 C15 -180(2) . . . . ? C18 C13 C14 N1 -177(2) . . . . ? C11 C13 C14 N1 4(3) . . . . ? N1 C14 C15 C16 175(2) . . . . ? C13 C14 C15 C16 0(3) . . . . ? C14 C15 C16 C17 1(3) . . . . ? C14 C15 C16 Cl1 173.6(19) . . . . ? C14 C15 C16 Cl1' -173(2) . . . . ? C15 C16 C17 C18 -1(4) . . . . ? Cl1 C16 C17 C18 -174(2) . . . . ? Cl1' C16 C17 C18 173(2) . . . . ? C16 C17 C18 C13 -1(3) . . . . ? C14 C13 C18 C17 2(3) . . . . ? C11 C13 C18 C17 180(2) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 17.22 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.905 _refine_diff_density_min -0.394 _refine_diff_density_rms 0.149 _database_code_depnum_ccdc_archive 'CCDC 888753'