# Electronic Supplementary Material (ESI) for Organic & Biomolecular 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_****** _audit_creation_method SHELXL-97 _chemical_name_systematic ; 5,6-dihydro-4H-benzo[f]naptho[2,1-c]chromen-4-one ; _chemical_name_common 'Annulated Coumarin' _chemical_melting_point 205 _chemical_formula_moiety 'C21 H14 O2' _chemical_formula_sum 'C21 H14 O2' _chemical_formula_weight 298.32 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' 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 Pbca 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' '-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 15.050(5) _cell_length_b 8.960(3) _cell_length_c 21.187(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2857.0(16) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2241 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 26.15 _exptl_crystal_description 'rectangular block' _exptl_crystal_colour Red _exptl_crystal_size_max 0.275 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.175 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.387 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1248 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 SMART APEX' _diffrn_measurement_method \q-2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_reflns_number 17307 _diffrn_reflns_av_R_equivalents 0.0861 _diffrn_reflns_av_sigmaI/netI 0.0764 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.35 _diffrn_reflns_theta_max 28.30 _reflns_number_total 3513 _reflns_number_gt 2408 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART 32(bruker)' _computing_cell_refinement 'SAINT (Bruker)' _computing_data_reduction 'SAINT (Bruker)' _computing_structure_solution 'SHELXTL (Bruker, 1997)' _computing_structure_refinement 'SHELXTL (Bruker, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 1997)' _computing_publication_material 'SHELXTL (Bruker, 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^)+(0.0894P)^2^+2.3153P] 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 SHELXL _refine_ls_extinction_coef 0.0036(14) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3513 _refine_ls_number_parameters 209 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1060 _refine_ls_R_factor_gt 0.0630 _refine_ls_wR_factor_ref 0.2040 _refine_ls_wR_factor_gt 0.1501 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_restrained_S_all 1.083 _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 C1 C -0.07067(15) 0.4755(3) 0.36401(11) 0.0262(5) Uani 1 1 d . . . H1 H -0.0437 0.4191 0.3312 0.031 Uiso 1 1 calc R . . C2 C -0.15989(16) 0.4618(3) 0.37458(12) 0.0299(6) Uani 1 1 d . . . H2 H -0.1938 0.3956 0.3492 0.036 Uiso 1 1 calc R . . C3 C -0.20235(17) 0.5442(3) 0.42260(12) 0.0324(6) Uani 1 1 d . . . H3 H -0.2647 0.5363 0.4285 0.039 Uiso 1 1 calc R . . C4 C -0.15297(16) 0.6358(3) 0.46068(12) 0.0302(6) Uani 1 1 d . . . H4 H -0.1814 0.6907 0.4933 0.036 Uiso 1 1 calc R . . C5 C -0.00832(17) 0.7366(3) 0.49454(11) 0.0285(5) Uani 1 1 d . . . H5 H -0.0373 0.7940 0.5261 0.034 Uiso 1 1 calc R . . C6 C 0.08162(16) 0.7386(3) 0.49064(11) 0.0284(5) Uani 1 1 d . . . H6 H 0.1160 0.7929 0.5204 0.034 Uiso 1 1 calc R . . C8 C 0.26372(16) 0.5604(3) 0.40757(11) 0.0268(5) Uani 1 1 d . . . C9 C 0.27376(15) 0.4029(3) 0.30829(11) 0.0253(5) Uani 1 1 d . . . H9A H 0.3176 0.3420 0.3317 0.030 Uiso 1 1 calc R . . H9B H 0.3066 0.4713 0.2799 0.030 Uiso 1 1 calc R . . C10 C 0.21358(15) 0.3016(3) 0.26946(11) 0.0262(5) Uani 1 1 d . . . H10A H 0.2488 0.2511 0.2363 0.031 Uiso 1 1 calc R . . H10B H 0.1872 0.2241 0.2970 0.031 Uiso 1 1 calc R . . C11 C 0.11513(15) 0.3781(3) 0.17654(11) 0.0265(5) Uani 1 1 d . . . H11 H 0.1427 0.3044 0.1509 0.032 Uiso 1 1 calc R . . C12 C 0.04962(16) 0.4698(3) 0.15075(11) 0.0280(5) Uani 1 1 d . . . H12 H 0.0316 0.4570 0.1081 0.034 Uiso 1 1 calc R . . C13 C 0.01098(16) 0.5801(3) 0.18777(11) 0.0272(5) Uani 1 1 d . . . H13 H -0.0323 0.6447 0.1700 0.033 Uiso 1 1 calc R . . C14 C 0.03521(15) 0.5965(3) 0.25068(11) 0.0262(5) Uani 1 1 d . . . H14 H 0.0088 0.6726 0.2756 0.031 Uiso 1 1 calc R . . C4A C -0.05967(16) 0.6497(3) 0.45200(11) 0.0260(5) Uani 1 1 d . . . C6A C 0.12308(15) 0.6587(3) 0.44163(11) 0.0250(5) Uani 1 1 d . . . C8A C 0.21829(15) 0.4923(3) 0.35417(11) 0.0243(5) Uani 1 1 d . . . C10A C 0.14066(15) 0.3930(2) 0.23944(11) 0.0235(5) Uani 1 1 d . . . C14A C 0.09860(15) 0.5009(2) 0.27733(11) 0.0231(5) Uani 1 1 d . . . C14B C 0.13090(15) 0.5219(2) 0.34321(11) 0.0225(5) Uani 1 1 d . . . C14C C 0.07729(15) 0.5864(2) 0.39387(10) 0.0221(5) Uani 1 1 d . . . C14D C -0.01755(15) 0.5727(2) 0.40112(10) 0.0234(5) Uani 1 1 d . . . O7 O 0.21454(10) 0.65709(19) 0.44448(8) 0.0274(4) Uani 1 1 d . . . O15 O 0.34196(11) 0.5497(2) 0.41939(9) 0.0351(5) 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 C1 0.0260(12) 0.0298(12) 0.0228(11) 0.0001(9) 0.0007(9) 0.0017(9) C2 0.0257(12) 0.0357(13) 0.0284(13) 0.0013(10) -0.0020(10) -0.0040(10) C3 0.0246(12) 0.0421(15) 0.0306(13) 0.0018(11) 0.0042(10) 0.0004(11) C4 0.0290(12) 0.0351(13) 0.0265(12) 0.0019(10) 0.0056(10) 0.0036(10) C5 0.0352(13) 0.0277(12) 0.0227(12) -0.0009(9) 0.0026(10) 0.0029(10) C6 0.0344(13) 0.0290(12) 0.0218(12) -0.0008(9) 0.0000(10) -0.0034(10) C8 0.0253(12) 0.0286(12) 0.0266(12) 0.0017(10) -0.0008(9) -0.0024(9) C9 0.0218(11) 0.0250(12) 0.0290(12) 0.0009(9) 0.0008(9) -0.0010(9) C10 0.0267(12) 0.0234(11) 0.0284(12) 0.0001(9) 0.0019(9) 0.0019(9) C11 0.0243(12) 0.0275(12) 0.0277(12) -0.0044(10) 0.0039(9) -0.0024(9) C12 0.0274(12) 0.0337(13) 0.0230(12) -0.0022(10) -0.0003(9) -0.0031(10) C13 0.0218(11) 0.0312(12) 0.0287(12) 0.0036(10) -0.0023(9) -0.0003(9) C14 0.0238(12) 0.0272(12) 0.0275(12) 0.0005(9) 0.0020(9) 0.0011(9) C4A 0.0304(12) 0.0270(12) 0.0208(11) 0.0031(9) 0.0025(9) 0.0012(9) C6A 0.0242(12) 0.0263(12) 0.0246(11) 0.0016(9) 0.0005(9) -0.0026(9) C8A 0.0246(12) 0.0251(11) 0.0233(12) 0.0034(9) 0.0001(9) -0.0021(9) C10A 0.0215(11) 0.0224(11) 0.0265(12) -0.0013(9) 0.0033(9) -0.0043(9) C14A 0.0214(11) 0.0236(11) 0.0242(12) 0.0008(9) 0.0008(9) -0.0014(8) C14B 0.0238(11) 0.0186(10) 0.0252(12) 0.0017(9) 0.0016(9) -0.0007(8) C14C 0.0238(11) 0.0226(11) 0.0198(11) 0.0022(8) -0.0003(9) 0.0003(8) C14D 0.0248(12) 0.0242(11) 0.0212(11) 0.0020(9) -0.0009(9) 0.0008(9) O7 0.0232(8) 0.0336(9) 0.0254(9) -0.0030(7) -0.0015(6) -0.0025(7) O15 0.0247(9) 0.0439(11) 0.0367(10) -0.0025(8) -0.0059(7) -0.0009(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 C1 C2 1.367(3) . ? C1 C14D 1.420(3) . ? C1 H1 0.9500 . ? C2 C3 1.410(4) . ? C2 H2 0.9500 . ? C3 C4 1.370(4) . ? C3 H3 0.9500 . ? C4 C4A 1.422(3) . ? C4 H4 0.9500 . ? C5 C6 1.356(4) . ? C5 C4A 1.420(3) . ? C5 H5 0.9500 . ? C6 C6A 1.407(3) . ? C6 H6 0.9500 . ? C8 O15 1.208(3) . ? C8 O7 1.382(3) . ? C8 C8A 1.456(3) . ? C9 C8A 1.511(3) . ? C9 C10 1.524(3) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C10A 1.510(3) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C10A 1.393(3) . ? C11 C12 1.395(3) . ? C11 H11 0.9500 . ? C12 C13 1.389(3) . ? C12 H12 0.9500 . ? C13 C14 1.390(3) . ? C13 H13 0.9500 . ? C14 C14A 1.401(3) . ? C14 H14 0.9500 . ? C4A C14D 1.428(3) . ? C6A O7 1.378(3) . ? C6A C14C 1.385(3) . ? C8A C14B 1.362(3) . ? C10A C14A 1.407(3) . ? C14A C14B 1.490(3) . ? C14B C14C 1.462(3) . ? C14C C14D 1.441(3) . ? 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 C14D 121.2(2) . . ? C2 C1 H1 119.4 . . ? C14D C1 H1 119.4 . . ? C1 C2 C3 121.1(2) . . ? C1 C2 H2 119.5 . . ? C3 C2 H2 119.5 . . ? C4 C3 C2 119.5(2) . . ? C4 C3 H3 120.2 . . ? C2 C3 H3 120.2 . . ? C3 C4 C4A 120.8(2) . . ? C3 C4 H4 119.6 . . ? C4A C4 H4 119.6 . . ? C6 C5 C4A 120.8(2) . . ? C6 C5 H5 119.6 . . ? C4A C5 H5 119.6 . . ? C5 C6 C6A 118.7(2) . . ? C5 C6 H6 120.6 . . ? C6A C6 H6 120.6 . . ? O15 C8 O7 117.0(2) . . ? O15 C8 C8A 125.9(2) . . ? O7 C8 C8A 116.8(2) . . ? C8A C9 C10 109.55(18) . . ? C8A C9 H9A 109.8 . . ? C10 C9 H9A 109.8 . . ? C8A C9 H9B 109.8 . . ? C10 C9 H9B 109.8 . . ? H9A C9 H9B 108.2 . . ? C10A C10 C9 109.65(19) . . ? C10A C10 H10A 109.7 . . ? C9 C10 H10A 109.7 . . ? C10A C10 H10B 109.7 . . ? C9 C10 H10B 109.7 . . ? H10A C10 H10B 108.2 . . ? C10A C11 C12 120.9(2) . . ? C10A C11 H11 119.6 . . ? C12 C11 H11 119.6 . . ? C13 C12 C11 119.6(2) . . ? C13 C12 H12 120.2 . . ? C11 C12 H12 120.2 . . ? C12 C13 C14 120.5(2) . . ? C12 C13 H13 119.8 . . ? C14 C13 H13 119.8 . . ? C13 C14 C14A 120.0(2) . . ? C13 C14 H14 120.0 . . ? C14A C14 H14 120.0 . . ? C5 C4A C4 120.2(2) . . ? C5 C4A C14D 120.2(2) . . ? C4 C4A C14D 119.6(2) . . ? O7 C6A C14C 121.6(2) . . ? O7 C6A C6 114.6(2) . . ? C14C C6A C6 123.8(2) . . ? C14B C8A C8 120.3(2) . . ? C14B C8A C9 121.8(2) . . ? C8 C8A C9 117.6(2) . . ? C11 C10A C14A 119.2(2) . . ? C11 C10A C10 123.5(2) . . ? C14A C10A C10 117.3(2) . . ? C14 C14A C10A 119.8(2) . . ? C14 C14A C14B 121.5(2) . . ? C10A C14A C14B 118.3(2) . . ? C8A C14B C14C 119.0(2) . . ? C8A C14B C14A 116.8(2) . . ? C14C C14B C14A 123.9(2) . . ? C6A C14C C14D 117.1(2) . . ? C6A C14C C14B 116.5(2) . . ? C14D C14C C14B 126.2(2) . . ? C1 C14D C4A 117.7(2) . . ? C1 C14D C14C 123.4(2) . . ? C4A C14D C14C 118.6(2) . . ? C6A O7 C8 121.12(18) . . ? 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 C14D C1 C2 C3 0.3(4) . . . . ? C1 C2 C3 C4 -2.2(4) . . . . ? C2 C3 C4 C4A 0.6(4) . . . . ? C4A C5 C6 C6A 3.1(4) . . . . ? C8A C9 C10 C10A 53.3(2) . . . . ? C10A C11 C12 C13 1.7(4) . . . . ? C11 C12 C13 C14 -1.9(4) . . . . ? C12 C13 C14 C14A -0.4(4) . . . . ? C6 C5 C4A C4 173.3(2) . . . . ? C6 C5 C4A C14D -5.2(3) . . . . ? C3 C4 C4A C5 -175.5(2) . . . . ? C3 C4 C4A C14D 3.0(4) . . . . ? C5 C6 C6A O7 -174.9(2) . . . . ? C5 C6 C6A C14C 5.0(4) . . . . ? O15 C8 C8A C14B -175.0(2) . . . . ? O7 C8 C8A C14B -1.5(3) . . . . ? O15 C8 C8A C9 -1.5(4) . . . . ? O7 C8 C8A C9 171.95(19) . . . . ? C10 C9 C8A C14B -24.9(3) . . . . ? C10 C9 C8A C8 161.8(2) . . . . ? C12 C11 C10A C14A 0.9(3) . . . . ? C12 C11 C10A C10 -177.4(2) . . . . ? C9 C10 C10A C11 134.6(2) . . . . ? C9 C10 C10A C14A -43.7(3) . . . . ? C13 C14 C14A C10A 3.0(3) . . . . ? C13 C14 C14A C14B 175.6(2) . . . . ? C11 C10A C14A C14 -3.2(3) . . . . ? C10 C10A C14A C14 175.2(2) . . . . ? C11 C10A C14A C14B -176.1(2) . . . . ? C10 C10A C14A C14B 2.4(3) . . . . ? C8 C8A C14B C14C -17.1(3) . . . . ? C9 C8A C14B C14C 169.7(2) . . . . ? C8 C8A C14B C14A 156.5(2) . . . . ? C9 C8A C14B C14A -16.7(3) . . . . ? C14 C14A C14B C8A -143.3(2) . . . . ? C10A C14A C14B C8A 29.4(3) . . . . ? C14 C14A C14B C14C 30.0(3) . . . . ? C10A C14A C14B C14C -157.4(2) . . . . ? O7 C6A C14C C14D 169.5(2) . . . . ? C6 C6A C14C C14D -10.4(3) . . . . ? O7 C6A C14C C14B -6.2(3) . . . . ? C6 C6A C14C C14B 173.9(2) . . . . ? C8A C14B C14C C6A 20.9(3) . . . . ? C14A C14B C14C C6A -152.2(2) . . . . ? C8A C14B C14C C14D -154.3(2) . . . . ? C14A C14B C14C C14D 32.6(3) . . . . ? C2 C1 C14D C4A 3.2(3) . . . . ? C2 C1 C14D C14C 177.1(2) . . . . ? C5 C4A C14D C1 173.7(2) . . . . ? C4 C4A C14D C1 -4.8(3) . . . . ? C5 C4A C14D C14C -0.5(3) . . . . ? C4 C4A C14D C14C -179.0(2) . . . . ? C6A C14C C14D C1 -166.0(2) . . . . ? C14B C14C C14D C1 9.2(3) . . . . ? C6A C14C C14D C4A 7.9(3) . . . . ? C14B C14C C14D C4A -176.9(2) . . . . ? C14C C6A O7 C8 -12.8(3) . . . . ? C6 C6A O7 C8 167.1(2) . . . . ? O15 C8 O7 C6A -169.2(2) . . . . ? C8A C8 O7 C6A 16.7(3) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.473 _refine_diff_density_min -0.496 _refine_diff_density_rms 0.126 _database_code_depnum_ccdc_archive 'CCDC 877580' ####################################################################### # # 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_***** _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3-amino-6,7-dichloro-5-hydroxybenzofuran-2,4-dicarbonitrile ; _chemical_name_common Benzofuran _chemical_melting_point 241 _chemical_formula_moiety 'C12 H6 Cl2 N4 O2' _chemical_formula_sum 'C12 H6 Cl2 N4 O2' _chemical_formula_weight 309.11 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 20.542(2) _cell_length_b 7.5120(10) _cell_length_c 18.182(2) _cell_angle_alpha 90.00 _cell_angle_beta 109.5930(10) _cell_angle_gamma 90.00 _cell_volume 2643.2(5) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1471 _cell_measurement_theta_min 3.2686 _cell_measurement_theta_max 32.4553 _exptl_crystal_description 'rectangular block' _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.150 _exptl_crystal_size_min 0.125 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.554 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1248 _exptl_absorpt_coefficient_mu 0.497 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.87144 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.0938 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8334 _diffrn_reflns_av_R_equivalents 0.0537 _diffrn_reflns_av_sigmaI/netI 0.0705 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 3.27 _diffrn_reflns_theta_max 32.53 _reflns_number_total 4295 _reflns_number_gt 2448 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_structure_solution 'SHELXTL-NT(Bruker, 1997)' _computing_structure_refinement 'SHELXTL-NT(Bruker, 1997)' _computing_molecular_graphics 'SHELXTL-NT(Bruker, 1997)' _computing_publication_material 'SHELXTL-NT(Bruker, 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^)+(0.0668P)^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_number_reflns 4295 _refine_ls_number_parameters 183 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1133 _refine_ls_R_factor_gt 0.0594 _refine_ls_wR_factor_ref 0.1660 _refine_ls_wR_factor_gt 0.1331 _refine_ls_goodness_of_fit_ref 0.993 _refine_ls_restrained_S_all 0.993 _refine_ls_shift/su_max 0.002 _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 C2 C 0.85204(12) 0.1105(3) 0.00149(14) 0.0371(6) Uani 1 1 d . . . C3 C 0.90209(11) 0.1889(3) 0.06264(14) 0.0339(5) Uani 1 1 d . . . C4 C 1.02411(11) 0.3016(3) 0.06503(13) 0.0307(5) Uani 1 1 d . . . C5 C 1.06555(11) 0.3179(3) 0.01756(13) 0.0335(5) Uani 1 1 d . . . C6 C 1.04014(11) 0.2585(3) -0.06059(14) 0.0336(5) Uani 1 1 d . . . C7 C 0.97545(11) 0.1819(3) -0.09183(13) 0.0318(5) Uani 1 1 d . . . C8 C 0.93517(10) 0.1677(3) -0.04409(13) 0.0307(5) Uani 1 1 d . . . C9 C 0.95774(10) 0.2269(3) 0.03253(12) 0.0296(5) Uani 1 1 d . . . C10 C 0.78684(12) 0.0444(4) -0.00304(15) 0.0442(6) Uani 1 1 d . . . C11 C 1.04967(12) 0.3646(4) 0.14407(14) 0.0384(6) Uani 1 1 d . . . C13 C 0.74450(16) 0.3375(5) 0.7614(2) 0.0663(9) Uani 1 1 d . . . C14 C 0.7731(2) 0.3351(6) 0.6990(2) 0.0783(11) Uani 1 1 d . . . H14A H 0.8031 0.2340 0.7051 0.117 Uiso 1 1 calc R . . H14B H 0.7990 0.4423 0.7006 0.117 Uiso 1 1 calc R . . H14C H 0.7364 0.3274 0.6498 0.117 Uiso 1 1 calc R . . Cl1 Cl 0.94464(4) 0.10260(10) -0.18560(4) 0.0487(2) Uani 1 1 d . . . Cl2 Cl 1.09143(3) 0.28719(11) -0.11730(4) 0.0517(2) Uani 1 1 d . . . N1 N 0.73479(11) -0.0094(4) -0.00312(14) 0.0619(7) Uani 1 1 d . . . N2 N 0.90134(11) 0.2194(3) 0.13548(13) 0.0488(6) Uani 1 1 d . . . H6A H 0.8661 0.1881 0.1480 0.059 Uiso 1 1 calc R . . H6B H 0.9361 0.2702 0.1694 0.059 Uiso 1 1 calc R . . N3 N 1.06813(13) 0.4134(3) 0.20684(13) 0.0562(7) Uani 1 1 d . . . N4 N 0.72296(19) 0.3340(6) 0.8104(2) 0.1065(13) Uani 1 1 d . . . O1 O 0.87109(8) 0.0952(2) -0.06558(9) 0.0364(4) Uani 1 1 d . . . O2 O 1.12813(9) 0.3912(3) 0.05090(10) 0.0480(5) Uani 1 1 d . . . H3 H 1.1496 0.3880 0.0202 0.072 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 C2 0.0232(10) 0.0452(15) 0.0479(13) -0.0037(12) 0.0185(10) -0.0046(10) C3 0.0262(11) 0.0395(13) 0.0399(12) 0.0016(11) 0.0161(9) -0.0023(10) C4 0.0237(10) 0.0360(13) 0.0328(11) 0.0014(10) 0.0100(8) -0.0046(10) C5 0.0221(10) 0.0396(13) 0.0394(12) 0.0065(11) 0.0112(9) -0.0029(10) C6 0.0264(10) 0.0399(14) 0.0397(12) 0.0055(10) 0.0181(9) 0.0002(10) C7 0.0270(10) 0.0373(13) 0.0319(11) 0.0021(10) 0.0112(9) -0.0008(10) C8 0.0171(9) 0.0383(13) 0.0373(11) 0.0025(10) 0.0100(8) -0.0002(9) C9 0.0219(9) 0.0344(12) 0.0351(11) 0.0035(10) 0.0131(8) -0.0019(9) C10 0.0265(11) 0.0547(16) 0.0552(15) -0.0085(13) 0.0186(11) -0.0076(12) C11 0.0301(12) 0.0440(15) 0.0411(13) 0.0070(11) 0.0119(10) -0.0048(11) C13 0.0470(18) 0.077(2) 0.080(2) 0.0031(19) 0.0283(17) -0.0048(17) C14 0.073(2) 0.098(3) 0.074(2) 0.001(2) 0.038(2) -0.005(2) Cl1 0.0471(4) 0.0650(5) 0.0348(3) -0.0042(3) 0.0149(3) -0.0067(3) Cl2 0.0427(4) 0.0713(5) 0.0531(4) 0.0006(3) 0.0322(3) -0.0128(3) N1 0.0335(12) 0.083(2) 0.0761(18) -0.0151(16) 0.0283(12) -0.0201(13) N2 0.0417(12) 0.0673(16) 0.0475(12) -0.0086(12) 0.0282(10) -0.0135(12) N3 0.0583(16) 0.0668(17) 0.0395(12) -0.0029(12) 0.0113(11) -0.0113(13) N4 0.090(3) 0.145(3) 0.113(3) -0.014(3) 0.072(2) -0.027(2) O1 0.0217(7) 0.0469(10) 0.0416(9) -0.0018(8) 0.0121(7) -0.0069(7) O2 0.0264(8) 0.0706(14) 0.0492(10) -0.0020(10) 0.0155(8) -0.0171(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 C2 C3 1.369(3) . ? C2 O1 1.405(3) . ? C2 C10 1.405(3) . ? C3 N2 1.349(3) . ? C3 C9 1.452(3) . ? C4 C5 1.406(3) . ? C4 C9 1.408(3) . ? C4 C11 1.435(3) . ? C5 O2 1.342(3) . ? C5 C6 1.412(3) . ? C6 C7 1.383(3) . ? C6 Cl2 1.717(2) . ? C7 C8 1.390(3) . ? C7 Cl1 1.714(2) . ? C8 O1 1.355(2) . ? C8 C9 1.386(3) . ? C10 N1 1.143(3) . ? C11 N3 1.136(3) . ? C13 N4 1.120(4) . ? C13 C14 1.443(5) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? N2 H6A 0.8600 . ? N2 H6B 0.8600 . ? O2 H3 0.8200 . ? 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 C3 C2 O1 112.85(19) . . ? C3 C2 C10 129.9(2) . . ? O1 C2 C10 117.2(2) . . ? N2 C3 C2 128.1(2) . . ? N2 C3 C9 127.3(2) . . ? C2 C3 C9 104.5(2) . . ? C5 C4 C9 118.5(2) . . ? C5 C4 C11 119.5(2) . . ? C9 C4 C11 121.97(19) . . ? O2 C5 C4 116.4(2) . . ? O2 C5 C6 124.00(19) . . ? C4 C5 C6 119.6(2) . . ? C7 C6 C5 121.65(19) . . ? C7 C6 Cl2 120.27(18) . . ? C5 C6 Cl2 118.07(17) . . ? C6 C7 C8 117.8(2) . . ? C6 C7 Cl1 122.44(16) . . ? C8 C7 Cl1 119.73(17) . . ? O1 C8 C9 112.57(18) . . ? O1 C8 C7 125.1(2) . . ? C9 C8 C7 122.3(2) . . ? C8 C9 C4 120.01(18) . . ? C8 C9 C3 106.00(19) . . ? C4 C9 C3 134.0(2) . . ? N1 C10 C2 176.9(3) . . ? N3 C11 C4 178.0(3) . . ? N4 C13 C14 177.8(5) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C3 N2 H6A 120.0 . . ? C3 N2 H6B 120.0 . . ? H6A N2 H6B 120.0 . . ? C8 O1 C2 104.08(17) . . ? C5 O2 H3 109.5 . . ? 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 C2 C3 N2 -178.1(2) . . . . ? C10 C2 C3 N2 1.3(5) . . . . ? O1 C2 C3 C9 0.0(3) . . . . ? C10 C2 C3 C9 179.4(3) . . . . ? C9 C4 C5 O2 179.4(2) . . . . ? C11 C4 C5 O2 0.9(3) . . . . ? C9 C4 C5 C6 -0.5(3) . . . . ? C11 C4 C5 C6 -179.0(2) . . . . ? O2 C5 C6 C7 179.2(2) . . . . ? C4 C5 C6 C7 -0.9(4) . . . . ? O2 C5 C6 Cl2 -1.8(3) . . . . ? C4 C5 C6 Cl2 178.07(19) . . . . ? C5 C6 C7 C8 1.2(4) . . . . ? Cl2 C6 C7 C8 -177.76(19) . . . . ? C5 C6 C7 Cl1 -177.93(19) . . . . ? Cl2 C6 C7 Cl1 3.2(3) . . . . ? C6 C7 C8 O1 -179.5(2) . . . . ? Cl1 C7 C8 O1 -0.4(3) . . . . ? C6 C7 C8 C9 -0.1(4) . . . . ? Cl1 C7 C8 C9 179.01(18) . . . . ? O1 C8 C9 C4 178.3(2) . . . . ? C7 C8 C9 C4 -1.2(4) . . . . ? O1 C8 C9 C3 -0.3(3) . . . . ? C7 C8 C9 C3 -179.8(2) . . . . ? C5 C4 C9 C8 1.5(3) . . . . ? C11 C4 C9 C8 -180.0(2) . . . . ? C5 C4 C9 C3 179.6(3) . . . . ? C11 C4 C9 C3 -1.9(4) . . . . ? N2 C3 C9 C8 178.3(2) . . . . ? C2 C3 C9 C8 0.2(3) . . . . ? N2 C3 C9 C4 0.0(5) . . . . ? C2 C3 C9 C4 -178.1(3) . . . . ? C3 C2 C10 N1 -17(6) . . . . ? O1 C2 C10 N1 163(6) . . . . ? C5 C4 C11 N3 176(9) . . . . ? C9 C4 C11 N3 -3(9) . . . . ? C9 C8 O1 C2 0.3(3) . . . . ? C7 C8 O1 C2 179.8(2) . . . . ? C3 C2 O1 C8 -0.1(3) . . . . ? C10 C2 O1 C8 -179.7(2) . . . . ? _diffrn_measured_fraction_theta_max 0.895 _diffrn_reflns_theta_full 32.53 _diffrn_measured_fraction_theta_full 0.895 _refine_diff_density_max 0.358 _refine_diff_density_min -0.317 _refine_diff_density_rms 0.074 #===END _database_code_depnum_ccdc_archive 'CCDC 877581'