# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2004 data_global _publ_contact_author_email DESIRAJU@UOHYD.ERNET.IN _publ_contact_author_name 'Prof Gautam Desiraju' _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_address ; School of Chemistry University of Hyderabad School of Chemistry, University of Hyderabad Andhra Pradesh 500 046 INDIA ; _publ_section_title ; Gauche and staggered forms of diethylamine in solvates of 1,5-dichloro-cis-9,10-diethynyl-9,10-dihydroanthracene-9,10-diol. A case of conformational pseudopolymorphism? ; loop_ _publ_author_name 'Gautam Desiraju' B.Rahul J.A.K.Howard 'Raju Mondal' data_02rmd056 _database_code_depnum_ccdc_archive 'CCDC 225589' _chemical_name_common ;Cis-1,5-dichloro-9,10-diethynyl-9,10-dihydroxy-9,10- dihydroanthracene ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; Cis-1,5-dichloro-9,10-diethynyl-9,10-dihydroxy-9,10-dihydroanthracene ; _chemical_melting_point ? _chemical_formula_moiety 'C18 H10 Cl2 O2' _chemical_formula_sum 'C18 H10 Cl2 O2' _chemical_formula_weight 329.16 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' 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 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 7.4731(2) _cell_length_b 12.5163(3) _cell_length_c 16.2952(5) _cell_angle_alpha 90.00 _cell_angle_beta 100.5650(10) _cell_angle_gamma 90.00 _cell_volume 1498.34(7) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 4365 _cell_measurement_theta_min 2.543 _cell_measurement_theta_max 27.403 _exptl_crystal_description Prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.459 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 672 _exptl_absorpt_coefficient_mu 0.436 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.892225 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'SADABS v.2.03 (Bruker, 2001), R(int)=0.1052 before correction' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 'smart 1k CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_decay_% 0 _diffrn_reflns_number 16656 _diffrn_reflns_av_R_equivalents 0.0626 _diffrn_reflns_av_sigmaI/netI 0.0524 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 27.47 _reflns_number_total 3431 _reflns_number_gt 2430 _reflns_threshold_expression I>2\s(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. ; _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^)+(0.0545P)^2^+1.0934P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3431 _refine_ls_number_parameters 239 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0848 _refine_ls_R_factor_gt 0.0539 _refine_ls_wR_factor_ref 0.1282 _refine_ls_wR_factor_gt 0.1172 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _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 0.06829(11) 0.04650(6) 0.33956(5) 0.0383(2) Uani 1 1 d . . . Cl2 Cl 0.74823(11) -0.47117(5) 0.39894(5) 0.0352(2) Uani 1 1 d . . . O1 O 0.3028(3) -0.08019(17) 0.24028(11) 0.0302(5) Uani 1 1 d . . . C12 C 0.5569(3) -0.2851(2) 0.35663(15) 0.0191(5) Uani 1 1 d . . . C13 C 0.2546(3) -0.1430(2) 0.37661(15) 0.0209(5) Uani 1 1 d . . . O2 O 0.3433(3) -0.41905(16) 0.38919(12) 0.0272(5) Uani 1 1 d . . . C14 C 0.2722(3) -0.2411(2) 0.41739(15) 0.0208(5) Uani 1 1 d . . . C11 C 0.5347(4) -0.1892(2) 0.31277(15) 0.0213(5) Uani 1 1 d . . . C10 C 0.4296(4) -0.31828(19) 0.41589(15) 0.0203(5) Uani 1 1 d . . . C9 C 0.3921(4) -0.1053(2) 0.32417(15) 0.0218(6) Uani 1 1 d . . . C5 C 0.7019(4) -0.3515(2) 0.34357(16) 0.0244(6) Uani 1 1 d . . . C1 C 0.1045(4) -0.0788(2) 0.38721(17) 0.0272(6) Uani 1 1 d . . . C6 C 0.8164(4) -0.3260(2) 0.28851(17) 0.0281(6) Uani 1 1 d . . . C8 C 0.6487(4) -0.1628(2) 0.25628(17) 0.0277(6) Uani 1 1 d . . . C17 C 0.5343(3) -0.32497(19) 0.50237(16) 0.0205(5) Uani 1 1 d . . . C15 C 0.4901(4) -0.0110(2) 0.36522(15) 0.0208(5) Uani 1 1 d . . . C2 C -0.0190(4) -0.1114(3) 0.43536(19) 0.0316(7) Uani 1 1 d . . . C4 C 0.1452(4) -0.2738(2) 0.46664(17) 0.0279(6) Uani 1 1 d . . . C16 C 0.5705(4) 0.0625(2) 0.39974(18) 0.0295(6) Uani 1 1 d . . . C18 C 0.6170(4) -0.3244(2) 0.57160(17) 0.0251(6) Uani 1 1 d . . . C7 C 0.7874(4) -0.2314(2) 0.24414(18) 0.0325(7) Uani 1 1 d . . . C3 C 0.0016(4) -0.2087(3) 0.47584(19) 0.0320(7) Uani 1 1 d . . . H8 H 0.638(4) -0.095(2) 0.2265(16) 0.022(7) Uiso 1 1 d . . . H1 H 0.247(6) -0.030(3) 0.240(2) 0.056(13) Uiso 1 1 d . . . H18 H 0.678(4) -0.323(2) 0.625(2) 0.037(9) Uiso 1 1 d . . . H2A H -0.113(4) -0.072(3) 0.4396(19) 0.036(9) Uiso 1 1 d . . . H2 H 0.409(5) -0.466(3) 0.408(2) 0.061(13) Uiso 1 1 d . . . H7 H 0.858(5) -0.212(3) 0.205(2) 0.052(10) Uiso 1 1 d . . . H3 H -0.080(4) -0.229(3) 0.509(2) 0.040(9) Uiso 1 1 d . . . H6 H 0.916(4) -0.377(3) 0.2851(19) 0.039(9) Uiso 1 1 d . . . H16 H 0.633(5) 0.115(3) 0.426(2) 0.046(10) Uiso 1 1 d . . . H4 H 0.132(4) -0.340(2) 0.4963(19) 0.030(8) 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 0.0385(4) 0.0327(4) 0.0415(4) 0.0052(3) 0.0021(3) 0.0156(3) Cl2 0.0485(5) 0.0237(4) 0.0364(4) 0.0046(3) 0.0156(3) 0.0130(3) O1 0.0444(13) 0.0269(11) 0.0151(9) 0.0026(8) -0.0055(8) 0.0064(10) C12 0.0225(13) 0.0194(12) 0.0148(12) -0.0031(10) 0.0016(10) -0.0010(11) C13 0.0194(13) 0.0217(13) 0.0190(12) -0.0022(10) -0.0035(10) -0.0010(10) O2 0.0345(12) 0.0169(9) 0.0283(10) -0.0013(8) 0.0008(8) -0.0079(9) C14 0.0173(12) 0.0246(13) 0.0189(13) -0.0033(10) -0.0010(10) -0.0051(10) C11 0.0272(14) 0.0218(13) 0.0140(12) -0.0037(10) 0.0017(10) -0.0036(11) C10 0.0270(14) 0.0158(12) 0.0175(13) -0.0014(9) 0.0024(10) -0.0038(10) C9 0.0286(14) 0.0203(13) 0.0140(12) 0.0021(10) -0.0025(10) 0.0010(11) C5 0.0338(15) 0.0182(13) 0.0206(13) -0.0021(10) 0.0032(11) 0.0016(11) C1 0.0241(14) 0.0272(14) 0.0271(14) -0.0025(11) -0.0041(11) 0.0021(12) C6 0.0342(16) 0.0264(14) 0.0268(15) -0.0079(11) 0.0139(12) 0.0017(13) C8 0.0375(17) 0.0251(15) 0.0222(14) 0.0015(11) 0.0102(12) -0.0030(12) C17 0.0230(14) 0.0183(12) 0.0216(13) 0.0024(10) 0.0079(11) 0.0007(10) C15 0.0250(14) 0.0206(13) 0.0168(12) 0.0042(10) 0.0042(10) 0.0028(11) C2 0.0146(14) 0.0402(18) 0.0381(17) -0.0073(13) -0.0005(12) 0.0047(13) C4 0.0256(15) 0.0303(15) 0.0276(15) 0.0017(12) 0.0047(12) -0.0063(12) C16 0.0350(17) 0.0259(15) 0.0261(15) -0.0025(12) 0.0020(12) -0.0007(13) C18 0.0297(15) 0.0258(14) 0.0194(14) 0.0021(11) 0.0032(12) -0.0014(12) C7 0.0395(18) 0.0332(16) 0.0289(15) -0.0039(12) 0.0172(13) -0.0034(14) C3 0.0206(15) 0.0425(18) 0.0338(16) -0.0032(13) 0.0071(12) -0.0072(13) _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(3) . ? Cl2 C5 1.750(3) . ? O1 C9 1.442(3) . ? O1 H1 0.76(4) . ? C12 C11 1.391(3) . ? C12 C5 1.412(4) . ? C12 C10 1.531(3) . ? C13 C14 1.390(4) . ? C13 C1 1.416(4) . ? C13 C9 1.527(4) . ? O2 C10 1.447(3) . ? O2 H2 0.78(4) . ? C14 C4 1.411(4) . ? C14 C10 1.526(4) . ? C11 C8 1.403(4) . ? C11 C9 1.531(4) . ? C10 C17 1.483(4) . ? C9 C15 1.482(4) . ? C5 C6 1.386(4) . ? C1 C2 1.378(4) . ? C6 C7 1.384(4) . ? C6 H6 0.99(3) . ? C8 C7 1.388(4) . ? C8 H8 0.97(3) . ? C17 C18 1.183(4) . ? C15 C16 1.183(4) . ? C2 C3 1.381(4) . ? C2 H2A 0.87(3) . ? C4 C3 1.377(4) . ? C4 H4 0.97(3) . ? C16 H16 0.87(4) . ? C18 H18 0.91(3) . ? C7 H7 0.93(4) . ? C3 H3 0.92(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 C9 O1 H1 110(3) . . ? C11 C12 C5 116.9(2) . . ? C11 C12 C10 121.9(2) . . ? C5 C12 C10 121.2(2) . . ? C14 C13 C1 116.8(2) . . ? C14 C13 C9 121.8(2) . . ? C1 C13 C9 121.5(2) . . ? C10 O2 H2 109(3) . . ? C13 C14 C4 120.9(2) . . ? C13 C14 C10 123.8(2) . . ? C4 C14 C10 115.2(2) . . ? C12 C11 C8 120.7(2) . . ? C12 C11 C9 123.3(2) . . ? C8 C11 C9 115.9(2) . . ? O2 C10 C17 111.4(2) . . ? O2 C10 C14 104.7(2) . . ? C17 C10 C14 107.1(2) . . ? O2 C10 C12 109.92(19) . . ? C17 C10 C12 109.5(2) . . ? C14 C10 C12 114.1(2) . . ? O1 C9 C15 111.0(2) . . ? O1 C9 C13 110.8(2) . . ? C15 C9 C13 108.7(2) . . ? O1 C9 C11 104.2(2) . . ? C15 C9 C11 107.7(2) . . ? C13 C9 C11 114.2(2) . . ? C6 C5 C12 123.0(2) . . ? C6 C5 Cl2 116.3(2) . . ? C12 C5 Cl2 120.7(2) . . ? C2 C1 C13 122.0(3) . . ? C2 C1 Cl1 116.9(2) . . ? C13 C1 Cl1 121.1(2) . . ? C7 C6 C5 118.6(3) . . ? C7 C6 H6 124.8(18) . . ? C5 C6 H6 116.6(18) . . ? C7 C8 C11 120.5(3) . . ? C7 C8 H8 117.5(16) . . ? C11 C8 H8 121.9(16) . . ? C18 C17 C10 176.4(3) . . ? C16 C15 C9 178.2(3) . . ? C1 C2 C3 120.4(3) . . ? C1 C2 H2A 121(2) . . ? C3 C2 H2A 119(2) . . ? C3 C4 C14 120.6(3) . . ? C3 C4 H4 107.4(18) . . ? C14 C4 H4 132.0(18) . . ? C15 C16 H16 178(2) . . ? C17 C18 H18 179(2) . . ? C6 C7 C8 120.3(3) . . ? C6 C7 H7 122(2) . . ? C8 C7 H7 118(2) . . ? C4 C3 C2 119.4(3) . . ? C4 C3 H3 121(2) . . ? C2 C3 H3 120(2) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.583 _refine_diff_density_min -0.347 _refine_diff_density_rms 0.064 data_02RMD059 _database_code_depnum_ccdc_archive 'CCDC 225590' _chemical_name_common ;Cis-1,5-dichloro-9,10-diethynyl-9,10-dihydroxy-9,10- dihydroanthracene ; _exptl_crystal_preparation Diethylamine _audit_creation_method SHELXL-97 _chemical_name_systematic ; Cis-1,5-dichloro-9,10-diethynyl-9,10-dihydroxy-9,10-dihydroanthracene ; _chemical_melting_point ? _chemical_formula_moiety (C18H10Cl2O2).(C4H11N) _chemical_formula_sum 'C22 H21 Cl2 N O2' _chemical_formula_weight 402.30 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' 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n 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 8.1794(2) _cell_length_b 13.6483(4) _cell_length_c 18.0272(5) _cell_angle_alpha 90.00 _cell_angle_beta 96.9840(10) _cell_angle_gamma 90.00 _cell_volume 1997.53(9) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 9622 _cell_measurement_theta_min 2.626 _cell_measurement_theta_max 27.482 _exptl_crystal_description cube _exptl_crystal_colour colourless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.338 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 840 _exptl_absorpt_coefficient_mu 0.342 _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 120(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 'smart 1k CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_decay_% 0 _diffrn_reflns_number 19907 _diffrn_reflns_av_R_equivalents 0.1289 _diffrn_reflns_av_sigmaI/netI 0.0648 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3925 _reflns_number_gt 3353 _reflns_threshold_expression I>2\s(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. ; _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^)+(0.0226P)^2^+1.4358P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3925 _refine_ls_number_parameters 328 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0572 _refine_ls_R_factor_gt 0.0460 _refine_ls_wR_factor_ref 0.1105 _refine_ls_wR_factor_gt 0.1063 _refine_ls_goodness_of_fit_ref 1.105 _refine_ls_restrained_S_all 1.105 _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 0.92773(7) -0.06018(4) 0.10067(3) 0.02590(15) Uani 1 1 d . . . Cl2 Cl 0.81282(8) 0.23486(4) 0.48693(3) 0.03059(17) Uani 1 1 d . . . O1 O 0.72683(16) -0.06068(10) 0.23343(8) 0.0164(3) Uani 1 1 d . . . O2 O 0.74568(17) 0.24876(10) 0.31840(8) 0.0182(3) Uani 1 1 d . . . C4 C 0.9648(2) 0.24249(15) 0.20045(12) 0.0188(4) Uani 1 1 d . . . C14 C 0.9308(2) 0.16417(14) 0.24635(11) 0.0160(4) Uani 1 1 d . . . C12 C 0.8593(2) 0.10428(14) 0.37424(11) 0.0153(4) Uani 1 1 d . . . C17 C 1.0399(3) 0.24683(14) 0.36144(12) 0.0204(4) Uani 1 1 d . . . C5 C 0.8191(3) 0.11802(15) 0.44767(12) 0.0203(4) Uani 1 1 d . . . C13 C 0.9224(2) 0.06831(14) 0.21839(11) 0.0152(4) Uani 1 1 d . . . C9 C 0.8793(2) -0.01850(14) 0.26647(11) 0.0154(4) Uani 1 1 d . . . C7 C 0.7886(3) -0.05481(17) 0.46564(13) 0.0246(5) Uani 1 1 d . . . C11 C 0.8583(2) 0.00823(14) 0.34767(11) 0.0157(4) Uani 1 1 d . . . C10 C 0.8937(2) 0.19147(14) 0.32545(11) 0.0154(4) Uani 1 1 d . . . C8 C 0.8253(3) -0.07066(15) 0.39385(12) 0.0203(4) Uani 1 1 d . . . C6 C 0.7848(3) 0.04088(17) 0.49267(13) 0.0254(5) Uani 1 1 d . . . C1 C 0.9466(2) 0.05529(15) 0.14290(12) 0.0196(4) Uani 1 1 d . . . C15 C 1.0119(2) -0.09324(14) 0.26860(12) 0.0190(4) Uani 1 1 d . . . C3 C 0.9923(3) 0.22716(16) 0.12703(13) 0.0231(5) Uani 1 1 d . . . C2 C 0.9835(3) 0.13266(16) 0.09765(12) 0.0235(5) Uani 1 1 d . . . C16 C 1.1221(3) -0.15031(16) 0.27304(15) 0.0277(5) Uani 1 1 d . . . C18 C 1.1611(3) 0.28901(18) 0.38543(15) 0.0327(6) Uani 1 1 d . . . N1 N 0.5239(2) 0.09381(13) 0.22078(10) 0.0191(4) Uani 1 1 d . . . C20 C 0.3679(3) 0.07196(17) 0.25071(13) 0.0236(5) Uani 1 1 d . . . C21 C 0.5010(3) 0.12665(17) 0.14215(13) 0.0267(5) Uani 1 1 d . . . C19 C 0.3944(3) 0.0626(2) 0.33520(15) 0.0352(6) Uani 1 1 d . . . C22 C 0.4415(4) 0.0448(2) 0.08873(15) 0.0403(7) Uani 1 1 d . . . H16 H 1.211(4) -0.190(2) 0.2772(18) 0.051(9) Uiso 1 1 d . . . H21B H 0.420(3) 0.1801(19) 0.1348(15) 0.032(7) Uiso 1 1 d . . . H19C H 0.293(4) 0.0500(19) 0.3522(15) 0.033(7) Uiso 1 1 d . . . H21A H 0.613(4) 0.151(2) 0.1307(17) 0.043(8) Uiso 1 1 d . . . H22C H 0.437(4) 0.068(2) 0.0364(18) 0.049(9) Uiso 1 1 d . . . H19B H 0.471(4) 0.007(2) 0.3513(16) 0.040(8) Uiso 1 1 d . . . H20B H 0.286(3) 0.1266(17) 0.2346(14) 0.024(6) Uiso 1 1 d . . . H20A H 0.323(3) 0.009(2) 0.2285(15) 0.036(7) Uiso 1 1 d . . . H19A H 0.444(4) 0.125(2) 0.3611(17) 0.043(8) Uiso 1 1 d . . . H22B H 0.516(4) -0.011(2) 0.0972(17) 0.045(8) Uiso 1 1 d . . . H111 H 0.572(4) 0.140(2) 0.2513(17) 0.043(8) Uiso 1 1 d . . . H22A H 0.324(4) 0.024(2) 0.0962(19) 0.059(10) Uiso 1 1 d . . . H1 H 0.646(4) -0.008(2) 0.2312(18) 0.054(9) Uiso 1 1 d . . . H2A H 0.996(3) 0.1220(18) 0.0495(15) 0.027(6) Uiso 1 1 d . . . H4 H 0.968(3) 0.3079(17) 0.2194(13) 0.016(5) Uiso 1 1 d . . . H7 H 0.766(3) -0.109(2) 0.4979(15) 0.034(7) Uiso 1 1 d . . . H3 H 1.016(3) 0.2829(18) 0.0959(14) 0.022(6) Uiso 1 1 d . . . H8 H 0.830(3) -0.1396(19) 0.3766(14) 0.027(6) Uiso 1 1 d . . . H6 H 0.758(3) 0.052(2) 0.5399(17) 0.039(8) Uiso 1 1 d . . . H18 H 1.257(4) 0.328(2) 0.4056(17) 0.051(9) Uiso 1 1 d . . . H2 H 0.766(4) 0.304(2) 0.3002(16) 0.041(8) 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 0.0356(3) 0.0206(3) 0.0225(3) -0.0070(2) 0.0077(2) 0.0002(2) Cl2 0.0495(4) 0.0221(3) 0.0210(3) -0.0066(2) 0.0077(2) -0.0015(2) O1 0.0146(7) 0.0125(6) 0.0212(8) -0.0023(6) -0.0018(6) -0.0007(6) O2 0.0191(7) 0.0116(7) 0.0242(8) 0.0022(6) 0.0036(6) 0.0022(6) C4 0.0184(10) 0.0145(10) 0.0240(11) 0.0022(8) 0.0042(8) -0.0003(8) C14 0.0105(9) 0.0160(9) 0.0209(10) 0.0023(8) 0.0000(8) 0.0009(7) C12 0.0140(9) 0.0151(9) 0.0158(10) 0.0012(8) -0.0018(7) 0.0001(7) C17 0.0221(11) 0.0148(10) 0.0236(11) 0.0000(8) 0.0001(9) 0.0000(8) C5 0.0234(10) 0.0169(10) 0.0199(11) -0.0021(8) -0.0003(8) -0.0001(8) C13 0.0117(9) 0.0141(9) 0.0193(10) -0.0002(8) 0.0002(7) 0.0003(7) C9 0.0138(9) 0.0121(9) 0.0200(11) -0.0013(8) 0.0012(8) 0.0004(7) C7 0.0293(11) 0.0237(11) 0.0202(11) 0.0084(9) 0.0004(9) -0.0039(9) C11 0.0139(9) 0.0161(9) 0.0161(10) 0.0009(8) -0.0029(8) 0.0001(7) C10 0.0148(9) 0.0115(9) 0.0192(10) -0.0001(8) 0.0000(8) -0.0003(7) C8 0.0219(10) 0.0152(10) 0.0228(11) 0.0044(8) -0.0006(8) -0.0002(8) C6 0.0314(12) 0.0280(12) 0.0168(11) 0.0024(9) 0.0026(9) -0.0010(9) C1 0.0177(10) 0.0171(10) 0.0236(11) -0.0024(9) 0.0017(8) 0.0010(8) C15 0.0181(10) 0.0144(10) 0.0244(11) 0.0010(8) 0.0019(8) -0.0041(8) C3 0.0251(11) 0.0201(10) 0.0251(12) 0.0074(9) 0.0072(9) 0.0010(9) C2 0.0265(11) 0.0284(12) 0.0163(11) 0.0007(9) 0.0056(9) 0.0040(9) C16 0.0206(11) 0.0198(11) 0.0433(14) 0.0044(10) 0.0059(10) 0.0031(9) C18 0.0309(13) 0.0252(12) 0.0400(15) -0.0028(11) -0.0033(11) -0.0068(10) N1 0.0185(9) 0.0186(9) 0.0200(9) 0.0010(7) 0.0013(7) 0.0002(7) C20 0.0193(10) 0.0215(11) 0.0296(12) 0.0041(9) 0.0019(9) 0.0004(9) C21 0.0336(13) 0.0235(11) 0.0231(12) 0.0052(9) 0.0034(10) 0.0100(10) C19 0.0278(13) 0.0461(16) 0.0332(14) 0.0064(12) 0.0102(11) 0.0022(12) C22 0.0616(19) 0.0329(14) 0.0235(13) -0.0026(11) -0.0064(12) 0.0173(14) _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 1.749(2) . ? Cl2 C5 1.748(2) . ? O1 C9 1.436(2) . ? O1 H1 0.98(3) . ? O2 C10 1.434(2) . ? O2 H2 0.85(3) . ? C4 C3 1.385(3) . ? C4 C14 1.400(3) . ? C4 H4 0.96(2) . ? C14 C13 1.401(3) . ? C14 C10 1.539(3) . ? C12 C11 1.395(3) . ? C12 C5 1.415(3) . ? C12 C10 1.526(3) . ? C17 C18 1.182(3) . ? C17 C10 1.495(3) . ? C5 C6 1.379(3) . ? C13 C1 1.410(3) . ? C13 C9 1.534(3) . ? C9 C15 1.486(3) . ? C9 C11 1.538(3) . ? C7 C8 1.381(3) . ? C7 C6 1.395(3) . ? C7 H7 0.97(3) . ? C11 C8 1.407(3) . ? C8 H8 0.99(3) . ? C6 H6 0.92(3) . ? C1 C2 1.390(3) . ? C15 C16 1.187(3) . ? C3 C2 1.393(3) . ? C3 H3 0.98(2) . ? C2 H2A 0.90(3) . ? C16 H16 0.91(3) . ? C18 H18 0.98(3) . ? N1 C20 1.475(3) . ? N1 C21 1.477(3) . ? N1 H111 0.89(3) . ? C20 C19 1.517(4) . ? C20 H20B 1.02(2) . ? C20 H20A 1.00(3) . ? C21 C22 1.516(4) . ? C21 H21B 0.99(3) . ? C21 H21A 1.02(3) . ? C19 H19C 0.93(3) . ? C19 H19B 1.01(3) . ? C19 H19A 1.03(3) . ? C22 H22C 0.99(3) . ? C22 H22B 0.98(3) . ? C22 H22A 1.03(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 C9 O1 H1 105.7(18) . . ? C10 O2 H2 109(2) . . ? C3 C4 C14 121.10(19) . . ? C3 C4 H4 118.9(14) . . ? C14 C4 H4 120.0(14) . . ? C4 C14 C13 120.32(19) . . ? C4 C14 C10 116.00(17) . . ? C13 C14 C10 123.57(17) . . ? C11 C12 C5 116.97(18) . . ? C11 C12 C10 121.90(18) . . ? C5 C12 C10 121.06(17) . . ? C18 C17 C10 175.2(3) . . ? C6 C5 C12 122.44(19) . . ? C6 C5 Cl2 116.13(17) . . ? C12 C5 Cl2 121.43(16) . . ? C14 C13 C1 117.29(18) . . ? C14 C13 C9 121.50(18) . . ? C1 C13 C9 121.12(17) . . ? O1 C9 C15 109.27(15) . . ? O1 C9 C13 108.85(15) . . ? C15 C9 C13 109.12(16) . . ? O1 C9 C11 107.33(15) . . ? C15 C9 C11 107.69(16) . . ? C13 C9 C11 114.48(16) . . ? C8 C7 C6 119.4(2) . . ? C8 C7 H7 121.5(16) . . ? C6 C7 H7 119.1(16) . . ? C12 C11 C8 120.61(19) . . ? C12 C11 C9 123.56(17) . . ? C8 C11 C9 115.67(17) . . ? O2 C10 C17 112.66(16) . . ? O2 C10 C12 105.29(15) . . ? C17 C10 C12 109.75(16) . . ? O2 C10 C14 108.02(15) . . ? C17 C10 C14 106.67(16) . . ? C12 C10 C14 114.58(16) . . ? C7 C8 C11 120.9(2) . . ? C7 C8 H8 117.6(15) . . ? C11 C8 H8 121.5(15) . . ? C5 C6 C7 119.6(2) . . ? C5 C6 H6 120.7(18) . . ? C7 C6 H6 119.6(18) . . ? C2 C1 C13 122.46(19) . . ? C2 C1 Cl1 116.31(17) . . ? C13 C1 Cl1 121.22(15) . . ? C16 C15 C9 176.7(2) . . ? C4 C3 C2 119.7(2) . . ? C4 C3 H3 119.7(14) . . ? C2 C3 H3 120.5(14) . . ? C1 C2 C3 119.0(2) . . ? C1 C2 H2A 120.2(16) . . ? C3 C2 H2A 120.7(16) . . ? C15 C16 H16 176(2) . . ? C17 C18 H18 175.8(18) . . ? C20 N1 C21 113.47(18) . . ? C20 N1 H111 104(2) . . ? C21 N1 H111 111.9(19) . . ? N1 C20 C19 111.08(19) . . ? N1 C20 H20B 108.3(14) . . ? C19 C20 H20B 110.9(14) . . ? N1 C20 H20A 108.7(16) . . ? C19 C20 H20A 109.2(16) . . ? H20B C20 H20A 109(2) . . ? N1 C21 C22 112.3(2) . . ? N1 C21 H21B 111.0(16) . . ? C22 C21 H21B 107.5(15) . . ? N1 C21 H21A 106.4(17) . . ? C22 C21 H21A 109.7(17) . . ? H21B C21 H21A 110(2) . . ? C20 C19 H19C 108.6(17) . . ? C20 C19 H19B 111.1(16) . . ? H19C C19 H19B 108(2) . . ? C20 C19 H19A 112.6(17) . . ? H19C C19 H19A 108(2) . . ? H19B C19 H19A 108(2) . . ? C21 C22 H22C 109.7(17) . . ? C21 C22 H22B 109.3(17) . . ? H22C C22 H22B 111(2) . . ? C21 C22 H22A 110.6(19) . . ? H22C C22 H22A 106(3) . . ? H22B C22 H22A 110(3) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.314 _refine_diff_density_min -0.289 _refine_diff_density_rms 0.071 data_03rmd069 _database_code_depnum_ccdc_archive 'CCDC 225591' _chemical_name_common ;Cis-1,5-dichloro-9,10-diethynyl-9,10-dihydroxy-9,10- dihydroanthracene ; _exptl_crystal_preparation Diethylamine _audit_creation_method SHELXL-97 _chemical_name_systematic ; Cis-1,5-dichloro-9,10-diethynyl-9,10-dihydroxy-9,10-dihydroanthracene ; _chemical_melting_point ? _chemical_formula_moiety (C18H10Cl2O2).(C4H11N) _chemical_formula_sum 'C22 H21 Cl2 N O2' _chemical_formula_weight 402.30 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 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 14.955(3) _cell_length_b 13.659(3) _cell_length_c 19.433(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3969.4(14) _cell_formula_units_Z 8 _cell_measurement_temperature 95(2) _cell_measurement_reflns_used 5095 _cell_measurement_theta_min 2.275 _cell_measurement_theta_max 27.282 _exptl_crystal_description Plate _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.346 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1680 _exptl_absorpt_coefficient_mu 0.344 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.871346 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'SADABS v.2.03 (Bruker, 2001), R(int)=0.0534 before correction' _exptl_special_details ; ? ; _diffrn_ambient_temperature 95(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 'Smart 1K CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean 8 _diffrn_standards_decay_% 0 _diffrn_reflns_number 41925 _diffrn_reflns_av_R_equivalents 0.0987 _diffrn_reflns_av_sigmaI/netI 0.0507 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 27.49 _reflns_number_total 4557 _reflns_number_gt 3539 _reflns_threshold_expression I>2\s(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. ; _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^)+(0.0397P)^2^+5.4094P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4557 _refine_ls_number_parameters 328 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0923 _refine_ls_R_factor_gt 0.0656 _refine_ls_wR_factor_ref 0.1315 _refine_ls_wR_factor_gt 0.1230 _refine_ls_goodness_of_fit_ref 1.161 _refine_ls_restrained_S_all 1.161 _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 0.29006(5) -0.10337(5) 0.18708(4) 0.02114(17) Uani 1 1 d . . . Cl2 Cl 0.39936(6) 0.23230(6) 0.52620(4) 0.0293(2) Uani 1 1 d . . . O2 O 0.27559(13) 0.22410(15) 0.39849(11) 0.0193(4) Uani 1 1 d . . . O1 O 0.24281(13) -0.08960(14) 0.34339(10) 0.0167(4) Uani 1 1 d . . . C15 C 0.39690(19) -0.1199(2) 0.31946(15) 0.0188(6) Uani 1 1 d . . . C7 C 0.3857(2) -0.0584(2) 0.52935(16) 0.0225(6) Uani 1 1 d . . . C17 C 0.43503(19) 0.2335(2) 0.37403(14) 0.0178(6) Uani 1 1 d . . . C5 C 0.38589(19) 0.1117(2) 0.49860(15) 0.0200(6) Uani 1 1 d . . . C14 C 0.33762(18) 0.1350(2) 0.30270(14) 0.0157(6) Uani 1 1 d . . . C8 C 0.3658(2) -0.0820(2) 0.46204(15) 0.0204(6) Uani 1 1 d . . . C6 C 0.3958(2) 0.0395(2) 0.54779(15) 0.0224(6) Uani 1 1 d . . . C2 C 0.30401(19) 0.0879(2) 0.16594(15) 0.0196(6) Uani 1 1 d . . . C12 C 0.36613(18) 0.0896(2) 0.42905(14) 0.0154(6) Uani 1 1 d . . . C3 C 0.3141(2) 0.1858(2) 0.18492(15) 0.0218(6) Uani 1 1 d . . . C16 C 0.4546(2) -0.1756(2) 0.30638(17) 0.0248(7) Uani 1 1 d . . . C4 C 0.33025(19) 0.2089(2) 0.25288(15) 0.0183(6) Uani 1 1 d . . . C10 C 0.35348(18) 0.17127(19) 0.37663(14) 0.0151(6) Uani 1 1 d . . . C18 C 0.5018(2) 0.2790(2) 0.36687(17) 0.0248(7) Uani 1 1 d . . . C9 C 0.32966(18) -0.04454(19) 0.33978(14) 0.0154(6) Uani 1 1 d . . . C11 C 0.35587(18) -0.0089(2) 0.41204(14) 0.0146(6) Uani 1 1 d . . . C1 C 0.30982(18) 0.0161(2) 0.21551(14) 0.0162(6) Uani 1 1 d . . . C13 C 0.32727(17) 0.0370(2) 0.28522(14) 0.0142(5) Uani 1 1 d . . . N1 N 0.11988(17) 0.05110(19) 0.37039(13) 0.0207(5) Uani 1 1 d . . . C21 C 0.0498(2) 0.0496(2) 0.31645(18) 0.0270(7) Uani 1 1 d . . . C20 C 0.0793(2) 0.0403(3) 0.43890(17) 0.0275(7) Uani 1 1 d . . . C22 C 0.0873(2) 0.0649(3) 0.2458(2) 0.0309(8) Uani 1 1 d . . . C19 C 0.1450(3) 0.0575(3) 0.49571(19) 0.0354(9) Uani 1 1 d . . . H111 H 0.146(2) 0.104(3) 0.3723(17) 0.024(9) Uiso 1 1 d . . . H8 H 0.358(2) -0.154(2) 0.4584(16) 0.023(8) Uiso 1 1 d . . . H21B H 0.001(2) 0.102(2) 0.3255(16) 0.026(9) Uiso 1 1 d . . . H21A H 0.021(2) -0.014(2) 0.3187(15) 0.015(7) Uiso 1 1 d . . . H20B H 0.053(2) -0.030(3) 0.4402(17) 0.030(9) Uiso 1 1 d . . . H6 H 0.412(2) 0.058(2) 0.5903(18) 0.026(9) Uiso 1 1 d . . . H16 H 0.501(2) -0.219(2) 0.2957(17) 0.026(9) Uiso 1 1 d . . . H4 H 0.334(2) 0.276(2) 0.2627(16) 0.020(8) Uiso 1 1 d . . . H2A H 0.293(2) 0.071(2) 0.1230(18) 0.024(9) Uiso 1 1 d . . . H7 H 0.396(2) -0.108(2) 0.5613(17) 0.022(8) Uiso 1 1 d . . . H22C H 0.121(2) 0.014(2) 0.2329(16) 0.021(9) Uiso 1 1 d . . . H3 H 0.314(2) 0.235(3) 0.1543(17) 0.028(9) Uiso 1 1 d . . . H20A H 0.026(2) 0.091(3) 0.4435(18) 0.035(10) Uiso 1 1 d . . . H19C H 0.165(3) 0.127(3) 0.495(2) 0.056(13) Uiso 1 1 d . . . H22B H 0.039(2) 0.067(2) 0.2114(17) 0.024(9) Uiso 1 1 d . . . H2 H 0.274(2) 0.276(3) 0.3807(19) 0.036(11) Uiso 1 1 d . . . H22A H 0.122(3) 0.128(3) 0.246(2) 0.043(11) Uiso 1 1 d . . . H19B H 0.192(3) 0.008(3) 0.493(2) 0.050(12) Uiso 1 1 d . . . H19A H 0.115(3) 0.055(3) 0.539(2) 0.039(10) Uiso 1 1 d . . . H18 H 0.553(3) 0.308(3) 0.362(2) 0.045(12) Uiso 1 1 d . . . H1 H 0.204(3) -0.044(3) 0.354(2) 0.065(14) 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 0.0232(4) 0.0202(3) 0.0200(3) -0.0051(3) 0.0010(3) -0.0011(3) Cl2 0.0431(5) 0.0263(4) 0.0184(3) -0.0073(3) 0.0035(3) -0.0039(3) O2 0.0195(11) 0.0162(10) 0.0223(10) 0.0031(9) 0.0088(9) 0.0052(8) O1 0.0115(9) 0.0145(10) 0.0240(10) 0.0001(8) 0.0020(8) -0.0018(8) C15 0.0199(14) 0.0175(14) 0.0190(14) 0.0017(11) 0.0012(12) 0.0005(11) C7 0.0178(15) 0.0275(16) 0.0221(15) 0.0122(13) 0.0004(13) 0.0012(12) C17 0.0219(15) 0.0161(13) 0.0154(13) -0.0008(11) 0.0019(12) 0.0019(11) C5 0.0172(14) 0.0234(15) 0.0194(14) -0.0004(12) 0.0028(12) 0.0002(12) C14 0.0106(13) 0.0189(13) 0.0175(14) 0.0018(11) 0.0020(11) 0.0017(10) C8 0.0188(15) 0.0211(15) 0.0215(15) 0.0076(12) 0.0023(12) 0.0026(12) C6 0.0190(16) 0.0346(17) 0.0136(14) -0.0004(12) 0.0022(12) 0.0031(13) C2 0.0181(15) 0.0254(16) 0.0154(14) -0.0007(12) 0.0015(11) 0.0012(12) C12 0.0114(13) 0.0177(13) 0.0171(13) 0.0001(11) 0.0035(11) 0.0003(10) C3 0.0222(15) 0.0263(16) 0.0170(14) 0.0068(13) 0.0044(12) 0.0050(12) C16 0.0238(16) 0.0242(15) 0.0262(16) -0.0005(13) 0.0022(14) 0.0062(13) C4 0.0180(15) 0.0147(13) 0.0223(14) 0.0022(12) 0.0040(12) 0.0001(11) C10 0.0157(14) 0.0126(12) 0.0171(13) 0.0009(11) 0.0042(11) 0.0011(10) C18 0.0230(17) 0.0245(16) 0.0270(16) 0.0021(13) 0.0022(14) -0.0035(13) C9 0.0137(13) 0.0125(12) 0.0199(14) -0.0002(11) 0.0009(11) 0.0000(10) C11 0.0098(13) 0.0184(13) 0.0157(13) 0.0016(11) 0.0032(10) 0.0027(10) C1 0.0133(14) 0.0182(13) 0.0171(14) -0.0030(11) 0.0012(11) 0.0012(10) C13 0.0078(12) 0.0200(14) 0.0147(13) 0.0008(11) 0.0022(10) 0.0011(10) N1 0.0187(13) 0.0190(13) 0.0243(13) -0.0012(11) 0.0082(11) -0.0024(10) C21 0.0165(15) 0.0240(16) 0.041(2) 0.0045(15) -0.0016(14) 0.0027(13) C20 0.0206(16) 0.0345(18) 0.0276(17) -0.0009(14) 0.0101(13) 0.0014(14) C22 0.0204(17) 0.0371(19) 0.0351(19) 0.0041(16) -0.0066(15) 0.0057(15) C19 0.0265(19) 0.055(3) 0.0247(18) 0.0037(17) 0.0086(15) -0.0018(18) _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 1.747(3) . ? Cl2 C5 1.743(3) . ? O2 C10 1.435(3) . ? O2 H2 0.79(4) . ? O1 C9 1.439(3) . ? O1 H1 0.88(5) . ? C15 C16 1.178(4) . ? C15 C9 1.492(4) . ? C7 C8 1.380(4) . ? C7 C6 1.392(4) . ? C7 H7 0.93(3) . ? C17 C18 1.184(4) . ? C17 C10 1.487(4) . ? C5 C6 1.382(4) . ? C5 C12 1.416(4) . ? C14 C13 1.390(4) . ? C14 C4 1.403(4) . ? C14 C10 1.538(4) . ? C8 C11 1.401(4) . ? C8 H8 0.99(3) . ? C6 H6 0.90(3) . ? C2 C1 1.378(4) . ? C2 C3 1.394(4) . ? C2 H2A 0.88(3) . ? C12 C11 1.394(4) . ? C12 C10 1.522(4) . ? C3 C4 1.379(4) . ? C3 H3 0.90(3) . ? C16 H16 0.93(3) . ? C4 H4 0.93(3) . ? C18 H18 0.87(4) . ? C9 C11 1.537(4) . ? C9 C13 1.538(4) . ? C1 C13 1.409(4) . ? N1 C20 1.471(4) . ? N1 C21 1.483(4) . ? N1 H111 0.83(3) . ? C21 C22 1.498(5) . ? C21 H21B 1.04(3) . ? C21 H21A 0.96(3) . ? C20 C19 1.496(5) . ? C20 H20B 1.04(3) . ? C20 H20A 1.06(4) . ? C22 H22C 0.90(3) . ? C22 H22B 0.98(3) . ? C22 H22A 1.01(4) . ? C19 H19C 1.00(4) . ? C19 H19B 0.98(4) . ? C19 H19A 0.95(4) . ? 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 C10 O2 H2 110(3) . . ? C9 O1 H1 107(3) . . ? C16 C15 C9 174.9(3) . . ? C8 C7 C6 119.5(3) . . ? C8 C7 H7 120(2) . . ? C6 C7 H7 120.4(19) . . ? C18 C17 C10 174.4(3) . . ? C6 C5 C12 122.0(3) . . ? C6 C5 Cl2 116.7(2) . . ? C12 C5 Cl2 121.3(2) . . ? C13 C14 C4 121.0(3) . . ? C13 C14 C10 123.8(2) . . ? C4 C14 C10 115.1(2) . . ? C7 C8 C11 120.9(3) . . ? C7 C8 H8 108.9(18) . . ? C11 C8 H8 130.2(19) . . ? C5 C6 C7 119.7(3) . . ? C5 C6 H6 118(2) . . ? C7 C6 H6 122(2) . . ? C1 C2 C3 119.4(3) . . ? C1 C2 H2A 119(2) . . ? C3 C2 H2A 122(2) . . ? C11 C12 C5 117.1(3) . . ? C11 C12 C10 122.3(2) . . ? C5 C12 C10 120.5(2) . . ? C4 C3 C2 119.4(3) . . ? C4 C3 H3 118(2) . . ? C2 C3 H3 123(2) . . ? C15 C16 H16 179(2) . . ? C3 C4 C14 120.6(3) . . ? C3 C4 H4 115.4(19) . . ? C14 C4 H4 124.0(19) . . ? O2 C10 C17 112.9(2) . . ? O2 C10 C12 105.7(2) . . ? C17 C10 C12 109.8(2) . . ? O2 C10 C14 108.3(2) . . ? C17 C10 C14 106.2(2) . . ? C12 C10 C14 114.1(2) . . ? C17 C18 H18 175(3) . . ? O1 C9 C15 109.0(2) . . ? O1 C9 C11 108.7(2) . . ? C15 C9 C11 106.8(2) . . ? O1 C9 C13 108.8(2) . . ? C15 C9 C13 109.4(2) . . ? C11 C9 C13 114.0(2) . . ? C12 C11 C8 120.8(3) . . ? C12 C11 C9 123.4(2) . . ? C8 C11 C9 115.8(2) . . ? C2 C1 C13 122.6(3) . . ? C2 C1 Cl1 115.7(2) . . ? C13 C1 Cl1 121.7(2) . . ? C14 C13 C1 116.8(2) . . ? C14 C13 C9 121.8(2) . . ? C1 C13 C9 121.3(2) . . ? C20 N1 C21 110.3(2) . . ? C20 N1 H111 104(2) . . ? C21 N1 H111 112(2) . . ? N1 C21 C22 112.4(3) . . ? N1 C21 H21B 111.8(18) . . ? C22 C21 H21B 108.9(18) . . ? N1 C21 H21A 107.1(18) . . ? C22 C21 H21A 109.4(18) . . ? H21B C21 H21A 107(3) . . ? N1 C20 C19 112.4(3) . . ? N1 C20 H20B 105.8(19) . . ? C19 C20 H20B 112.2(19) . . ? N1 C20 H20A 108.9(19) . . ? C19 C20 H20A 109.4(19) . . ? H20B C20 H20A 108(3) . . ? C21 C22 H22C 111(2) . . ? C21 C22 H22B 110.6(19) . . ? H22C C22 H22B 104(3) . . ? C21 C22 H22A 108(2) . . ? H22C C22 H22A 112(3) . . ? H22B C22 H22A 111(3) . . ? C20 C19 H19C 110(2) . . ? C20 C19 H19B 109(2) . . ? H19C C19 H19B 116(4) . . ? C20 C19 H19A 110(2) . . ? H19C C19 H19A 101(3) . . ? H19B C19 H19A 111(3) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.641 _refine_diff_density_min -0.323 _refine_diff_density_rms 0.071