# Electronic Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 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_2c _database_code_depnum_ccdc_archive 'CCDC 847587' #TrackingRef 'CIF combined.cif' _audit_creation_date 2012-10-28 _audit_creation_method ; Olex2 1.2 (compiled 2012.05.09 svn.r2324, GUI svn.r4230) ; _chemical_name_common (4-(Diethylamino)phenyl)(pyridine-2-yl)methanol _chemical_name_systematic ; (4-(Diethylamino)phenyl)(pyridine-2-yl)methanol ; _chemical_formula_moiety 'C16 H20 N2 O' _chemical_formula_sum 'C16 H20 N2 O' _chemical_formula_weight 256.34 _chemical_melting_point 365 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' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x, -y-1/2, z-1/2' _cell_length_a 11.7951(6) _cell_length_b 9.4577(5) _cell_length_c 12.8525(7) _cell_angle_alpha 90.00 _cell_angle_beta 91.093(5) _cell_angle_gamma 90.00 _cell_volume 1433.49(13) _cell_formula_units_Z 4 _cell_measurement_reflns_used 4557 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 29.1046 _cell_measurement_theta_min 2.6673 _exptl_absorpt_coefficient_mu 0.075 _exptl_absorpt_correction_T_max 0.979 _exptl_absorpt_correction_T_min 0.969 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.188 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 552 _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.25 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0337 _diffrn_reflns_av_unetI/netI 0.0250 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 11281 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 2.67 _diffrn_ambient_temperature 298(2) _diffrn_detector_area_resol_mean 15.9821 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -85.00 10.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - -17.4178 0.0000 150.0000 95 #__ type_ start__ end____ width___ exp.time_ 2 omega -69.00 6.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - -17.4178 -37.0000 -120.0000 75 #__ type_ start__ end____ width___ exp.time_ 3 omega -88.00 -1.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - -17.4178 -37.0000 -30.0000 87 #__ type_ start__ end____ width___ exp.time_ 4 omega -24.00 49.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - -17.4178 37.0000 0.0000 73 #__ type_ start__ end____ width___ exp.time_ 5 omega 68.00 95.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - 19.1366 179.0000 120.0000 27 #__ type_ start__ end____ width___ exp.time_ 6 omega -80.00 -3.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - -17.4178 134.0000 152.0000 77 #__ type_ start__ end____ width___ exp.time_ 7 omega -11.00 21.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - 19.1366 77.0000 120.0000 32 ; _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0485121000 _diffrn_orient_matrix_UB_12 0.0278274000 _diffrn_orient_matrix_UB_13 -0.0262470000 _diffrn_orient_matrix_UB_21 -0.0247851000 _diffrn_orient_matrix_UB_22 0.0153267000 _diffrn_orient_matrix_UB_23 0.0485264000 _diffrn_orient_matrix_UB_31 0.0254218000 _diffrn_orient_matrix_UB_32 0.0678925000 _diffrn_orient_matrix_UB_33 -0.0002053000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 1889 _reflns_number_total 2522 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; SHELXS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.352 _refine_diff_density_min -0.285 _refine_diff_density_rms 0.038 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 178 _refine_ls_number_reflns 2522 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0774 _refine_ls_R_factor_gt 0.0584 _refine_ls_restrained_S_all 1.044 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0731P)^2^+0.7174P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1545 _refine_ls_wR_factor_ref 0.1701 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.45848(16) 0.2690(2) 0.61122(17) 0.0407(5) Uani 1 1 d . . . C7 C 0.65582(18) 0.2219(2) 0.67064(16) 0.0419(5) Uani 1 1 d . . . C6 C 0.53248(18) 0.1846(2) 0.68617(17) 0.0446(5) Uani 1 1 d . . . H6 H 0.5120 0.2084 0.7576 0.053 Uiso 1 1 calc R . . O1 O 0.50994(16) 0.03891(16) 0.66839(15) 0.0614(5) Uani 1 1 d . . . C8 C 0.7153(2) 0.3073(3) 0.73962(17) 0.0520(6) Uani 1 1 d . . . H8 H 0.6796 0.3393 0.7991 0.062 Uiso 1 1 calc R . . C11 C 0.8226(2) 0.2163(3) 0.5647(2) 0.0595(7) Uani 1 1 d . . . H11 H 0.8578 0.1831 0.5053 0.071 Uiso 1 1 calc R . . C10 C 0.8833(2) 0.3047(3) 0.6332(2) 0.0592(7) Uani 1 1 d . . . C3 C 0.3672(2) 0.3044(3) 0.4470(2) 0.0600(7) Uani 1 1 d . . . H3 H 0.3459 0.2724 0.3810 0.072 Uiso 1 1 calc R . . C12 C 0.71271(19) 0.1777(2) 0.58293(19) 0.0514(6) Uani 1 1 d . . . H12 H 0.6751 0.1200 0.5349 0.062 Uiso 1 1 calc R . . C4 C 0.3378(2) 0.4379(3) 0.4787(2) 0.0625(7) Uani 1 1 d . . . H4 H 0.2974 0.4984 0.4347 0.075 Uiso 1 1 calc R . . C5 C 0.3697(2) 0.4789(3) 0.5765(2) 0.0617(7) Uani 1 1 d . . . H5 H 0.3491 0.5690 0.5981 0.074 Uiso 1 1 calc R . . C9 C 0.8264(2) 0.3467(3) 0.72284(19) 0.0608(7) Uani 1 1 d . . . H9 H 0.8641 0.4022 0.7721 0.073 Uiso 1 1 calc R . . N2 N 0.99222(19) 0.3507(3) 0.6120(2) 0.0877(8) Uani 1 1 d . . . C13 C 1.0564(3) 0.2859(4) 0.5296(3) 0.0887(10) Uani 1 1 d . . . H13A H 1.1165 0.3501 0.5102 0.106 Uiso 1 1 calc R . . H13B H 1.0068 0.2737 0.4693 0.106 Uiso 1 1 calc R . . C15 C 1.0524(3) 0.4575(5) 0.6786(3) 0.1045(13) Uani 1 1 d . . . H15A H 1.1016 0.5142 0.6357 0.125 Uiso 1 1 calc R . . H15B H 0.9971 0.5201 0.7093 0.125 Uiso 1 1 calc R . . C16 C 1.1179(5) 0.3928(6) 0.7587(4) 0.1460(18) Uani 1 1 d . . . H16A H 1.0685 0.3461 0.8063 0.219 Uiso 1 1 calc R . . H16B H 1.1613 0.4635 0.7953 0.219 Uiso 1 1 calc R . . H16C H 1.1682 0.3248 0.7289 0.219 Uiso 1 1 calc R . . C14 C 1.1077(3) 0.1466(4) 0.5567(4) 0.1127(13) Uani 1 1 d . . . H14A H 1.0489 0.0814 0.5749 0.169 Uiso 1 1 calc R . . H14B H 1.1595 0.1577 0.6147 0.169 Uiso 1 1 calc R . . H14C H 1.1478 0.1107 0.4980 0.169 Uiso 1 1 calc R . . N1 N 0.42867(15) 0.39814(19) 0.64349(16) 0.0501(5) Uani 1 1 d . . . C2 C 0.42810(19) 0.2188(2) 0.51348(18) 0.0504(6) Uani 1 1 d . . . H2 H 0.4488 0.1282 0.4932 0.061 Uiso 1 1 calc R . . H1 H 0.536(3) -0.012(3) 0.733(3) 0.089(9) 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 C1 0.0351(10) 0.0385(11) 0.0488(12) -0.0008(9) 0.0104(9) -0.0062(9) C7 0.0443(12) 0.0374(11) 0.0441(12) 0.0031(9) 0.0018(9) 0.0050(9) C6 0.0502(13) 0.0379(11) 0.0458(12) 0.0009(9) 0.0068(10) -0.0034(9) O1 0.0767(12) 0.0397(9) 0.0677(12) 0.0072(8) -0.0021(9) -0.0110(8) C8 0.0540(14) 0.0612(14) 0.0409(13) -0.0038(11) 0.0048(10) 0.0011(11) C11 0.0464(13) 0.0729(17) 0.0594(15) -0.0142(13) 0.0090(11) 0.0070(12) C10 0.0426(13) 0.0722(17) 0.0627(16) -0.0039(13) 0.0030(11) 0.0021(12) C3 0.0455(13) 0.0824(19) 0.0521(14) 0.0016(13) 0.0003(11) -0.0082(13) C12 0.0477(13) 0.0513(13) 0.0552(14) -0.0116(11) 0.0017(11) 0.0030(10) C4 0.0419(13) 0.0678(17) 0.0778(19) 0.0237(15) -0.0002(12) -0.0007(12) C5 0.0511(14) 0.0441(13) 0.090(2) 0.0011(13) 0.0008(14) 0.0040(11) C9 0.0533(14) 0.0762(17) 0.0526(15) -0.0092(13) -0.0061(12) -0.0074(13) N2 0.0458(12) 0.121(2) 0.0965(19) -0.0247(17) 0.0114(12) -0.0144(13) C13 0.0516(16) 0.117(3) 0.099(2) -0.003(2) 0.0239(16) -0.0069(17) C15 0.0568(18) 0.156(4) 0.101(3) -0.016(3) 0.0066(18) -0.017(2) C16 0.145(4) 0.164(5) 0.128(4) 0.005(3) -0.015(3) -0.023(4) C14 0.075(2) 0.120(3) 0.144(4) 0.003(3) 0.023(2) 0.007(2) N1 0.0458(11) 0.0408(10) 0.0638(12) -0.0050(9) 0.0028(9) -0.0002(8) C2 0.0471(13) 0.0510(13) 0.0534(14) -0.0069(11) 0.0050(11) -0.0020(10) _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 C6 1.515(3) . ? C1 N1 1.339(3) . ? C1 C2 1.384(3) . ? C7 C6 1.514(3) . ? C7 C8 1.381(3) . ? C7 C12 1.387(3) . ? C6 H6 0.9800 . ? C6 O1 1.421(3) . ? O1 H1 1.00(3) . ? C8 H8 0.9300 . ? C8 C9 1.383(3) . ? C11 H11 0.9300 . ? C11 C10 1.401(4) . ? C11 C12 1.372(3) . ? C10 C9 1.402(4) . ? C10 N2 1.389(3) . ? C3 H3 0.9300 . ? C3 C4 1.373(4) . ? C3 C2 1.371(3) . ? C12 H12 0.9300 . ? C4 H4 0.9300 . ? C4 C5 1.362(4) . ? C5 H5 0.9300 . ? C5 N1 1.336(3) . ? C9 H9 0.9300 . ? N2 C13 1.449(4) . ? N2 C15 1.495(4) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C13 C14 1.489(5) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C15 C16 1.414(6) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C2 H2 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 N1 C1 C6 115.81(19) . . ? N1 C1 C2 121.9(2) . . ? C2 C1 C6 122.17(19) . . ? C8 C7 C6 122.0(2) . . ? C8 C7 C12 116.7(2) . . ? C12 C7 C6 121.2(2) . . ? C1 C6 H6 109.0 . . ? C7 C6 C1 109.68(17) . . ? C7 C6 H6 109.0 . . ? O1 C6 C1 107.76(18) . . ? O1 C6 C7 112.48(18) . . ? O1 C6 H6 109.0 . . ? C6 O1 H1 105.9(18) . . ? C7 C8 H8 119.0 . . ? C7 C8 C9 121.9(2) . . ? C9 C8 H8 119.0 . . ? C10 C11 H11 119.2 . . ? C12 C11 H11 119.2 . . ? C12 C11 C10 121.6(2) . . ? C11 C10 C9 116.1(2) . . ? N2 C10 C11 121.8(2) . . ? N2 C10 C9 122.2(2) . . ? C4 C3 H3 120.3 . . ? C2 C3 H3 120.3 . . ? C2 C3 C4 119.4(2) . . ? C7 C12 H12 118.9 . . ? C11 C12 C7 122.2(2) . . ? C11 C12 H12 118.9 . . ? C3 C4 H4 121.0 . . ? C5 C4 C3 118.0(2) . . ? C5 C4 H4 121.0 . . ? C4 C5 H5 117.9 . . ? N1 C5 C4 124.3(2) . . ? N1 C5 H5 117.9 . . ? C8 C9 C10 121.5(2) . . ? C8 C9 H9 119.3 . . ? C10 C9 H9 119.3 . . ? C10 N2 C13 120.6(3) . . ? C10 N2 C15 122.0(2) . . ? C13 N2 C15 117.1(2) . . ? N2 C13 H13A 108.6 . . ? N2 C13 H13B 108.6 . . ? N2 C13 C14 114.8(3) . . ? H13A C13 H13B 107.5 . . ? C14 C13 H13A 108.6 . . ? C14 C13 H13B 108.6 . . ? N2 C15 H15A 109.3 . . ? N2 C15 H15B 109.3 . . ? H15A C15 H15B 107.9 . . ? C16 C15 N2 111.8(4) . . ? C16 C15 H15A 109.3 . . ? C16 C15 H15B 109.3 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16B 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14B 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C5 N1 C1 117.3(2) . . ? C1 C2 H2 120.4 . . ? C3 C2 C1 119.1(2) . . ? C3 C2 H2 120.4 . . ? 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 C7 C8 C9 C10 1.7(4) . . . . ? C6 C1 N1 C5 175.69(19) . . . . ? C6 C1 C2 C3 -175.7(2) . . . . ? C6 C7 C8 C9 -176.9(2) . . . . ? C6 C7 C12 C11 176.6(2) . . . . ? C8 C7 C6 C1 104.6(2) . . . . ? C8 C7 C6 O1 -135.5(2) . . . . ? C8 C7 C12 C11 -0.1(3) . . . . ? C11 C10 C9 C8 -2.6(4) . . . . ? C11 C10 N2 C13 -13.2(5) . . . . ? C11 C10 N2 C15 173.0(3) . . . . ? C10 C11 C12 C7 -0.9(4) . . . . ? C10 N2 C13 C14 -77.9(4) . . . . ? C10 N2 C15 C16 91.4(4) . . . . ? C3 C4 C5 N1 0.6(4) . . . . ? C12 C7 C6 C1 -71.9(2) . . . . ? C12 C7 C6 O1 48.0(3) . . . . ? C12 C7 C8 C9 -0.3(3) . . . . ? C12 C11 C10 C9 2.2(4) . . . . ? C12 C11 C10 N2 -176.2(3) . . . . ? C4 C3 C2 C1 0.1(3) . . . . ? C4 C5 N1 C1 0.4(3) . . . . ? C9 C10 N2 C13 168.6(3) . . . . ? C9 C10 N2 C15 -5.2(5) . . . . ? N2 C10 C9 C8 175.8(3) . . . . ? C13 N2 C15 C16 -82.6(4) . . . . ? C15 N2 C13 C14 96.2(4) . . . . ? N1 C1 C6 C7 -85.9(2) . . . . ? N1 C1 C6 O1 151.31(18) . . . . ? N1 C1 C2 C3 1.0(3) . . . . ? C2 C1 C6 C7 91.0(2) . . . . ? C2 C1 C6 O1 -31.7(3) . . . . ? C2 C1 N1 C5 -1.3(3) . . . . ? C2 C3 C4 C5 -0.9(4) . . . . ? data_2a _database_code_depnum_ccdc_archive 'CCDC 847589' #TrackingRef 'CIF combined.cif' _audit_creation_date 2012-10-28 _audit_creation_method ; Olex2 1.2 (compiled 2012.05.09 svn.r2324, GUI svn.r4230) ; _chemical_name_common (4-Methoxyphenyl)(pyridine-2-yl)methanol _chemical_name_systematic ; (4-Methoxyphenyl)(pyridine-2-yl)methanol ; _chemical_formula_moiety 'C13 H13 N O2' _chemical_formula_sum 'C13 H13 N O2' _chemical_formula_weight 215.24 _chemical_melting_point 409 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' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x, -y-1/2, z-1/2' _cell_length_a 8.4890(3) _cell_length_b 17.2434(6) _cell_length_c 8.1339(3) _cell_angle_alpha 90.00 _cell_angle_beta 110.610(4) _cell_angle_gamma 90.00 _cell_volume 1114.43(7) _cell_formula_units_Z 4 _cell_measurement_reflns_used 3092 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 29.1168 _cell_measurement_theta_min 2.6700 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_T_max 0.982 _exptl_absorpt_correction_T_min 0.966 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.283 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 456 _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.2 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0209 _diffrn_reflns_av_unetI/netI 0.0275 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_number 4704 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 2.82 _diffrn_ambient_temperature 150(2) _diffrn_detector_area_resol_mean 15.9821 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -93.00 -64.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - -17.3397 179.0000 0.0000 29 #__ type_ start__ end____ width___ exp.time_ 2 omega -69.00 12.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - -17.3397 -77.0000 0.0000 81 #__ type_ start__ end____ width___ exp.time_ 3 omega -34.00 75.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 19.0585 0.0000 -180.0000 109 #__ type_ start__ end____ width___ exp.time_ 4 omega -7.00 18.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 19.0585 37.0000 -120.0000 25 ; _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0380675000 _diffrn_orient_matrix_UB_12 -0.0315719000 _diffrn_orient_matrix_UB_13 0.0276322000 _diffrn_orient_matrix_UB_21 0.0669432000 _diffrn_orient_matrix_UB_22 -0.0245235000 _diffrn_orient_matrix_UB_23 -0.0004905000 _diffrn_orient_matrix_UB_31 0.0451808000 _diffrn_orient_matrix_UB_32 0.0096611000 _diffrn_orient_matrix_UB_33 0.0890049000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_source_current ? _diffrn_source_voltage ? _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 1693 _reflns_number_total 1965 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; SHELXS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.179 _refine_diff_density_min -0.179 _refine_diff_density_rms 0.037 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 150 _refine_ls_number_reflns 1965 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0430 _refine_ls_R_factor_gt 0.0353 _refine_ls_restrained_S_all 1.042 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0338P)^2^+0.3186P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0793 _refine_ls_wR_factor_ref 0.0838 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 O2 O 0.19605(12) 0.66805(6) 1.14433(12) 0.0221(2) Uani 1 1 d . . . O1 O -0.29664(12) 0.52080(6) 0.44430(13) 0.0319(3) Uani 1 1 d . . . N1 N 0.41922(13) 0.71664(6) 0.85472(14) 0.0189(3) Uani 1 1 d . . . C5 C 0.07008(15) 0.64286(8) 0.83648(16) 0.0166(3) Uani 1 1 d . . . C7 C -0.06468(16) 0.51987(8) 0.72628(18) 0.0214(3) Uani 1 1 d . . . H7 H -0.0729 0.4655 0.7410 0.026 Uiso 1 1 calc R . . C9 C 0.37594(16) 0.67348(7) 0.96937(16) 0.0163(3) Uani 1 1 d . . . C8 C 0.20229(16) 0.68885(8) 0.97727(16) 0.0172(3) Uani 1 1 d . . . H8 H 0.1763 0.7454 0.9569 0.021 Uiso 1 1 calc R . . C6 C 0.05533(16) 0.56340(8) 0.85355(17) 0.0196(3) Uani 1 1 d . . . H6 H 0.1293 0.5380 0.9551 0.023 Uiso 1 1 calc R . . C2 C -0.17218(16) 0.55667(8) 0.57763(17) 0.0218(3) Uani 1 1 d . . . C3 C -0.15823(18) 0.63618(9) 0.55799(18) 0.0270(3) Uani 1 1 d . . . H3 H -0.2313 0.6614 0.4558 0.032 Uiso 1 1 calc R . . C10 C 0.48190(17) 0.61750(8) 1.07387(18) 0.0226(3) Uani 1 1 d . . . H10 H 0.4480 0.5879 1.1542 0.027 Uiso 1 1 calc R . . C13 C 0.56986(16) 0.70313(8) 0.84099(18) 0.0231(3) Uani 1 1 d . . . H13 H 0.6005 0.7327 0.7584 0.028 Uiso 1 1 calc R . . C11 C 0.63751(17) 0.60537(8) 1.05950(18) 0.0260(3) Uani 1 1 d . . . H11 H 0.7125 0.5677 1.1307 0.031 Uiso 1 1 calc R . . C4 C -0.03874(17) 0.67873(8) 0.68622(18) 0.0229(3) Uani 1 1 d . . . H4 H -0.0308 0.7331 0.6716 0.027 Uiso 1 1 calc R . . C12 C 0.68246(17) 0.64879(9) 0.93998(18) 0.0258(3) Uani 1 1 d . . . H12 H 0.7881 0.6414 0.9265 0.031 Uiso 1 1 calc R . . C1 C -0.3139(2) 0.43919(9) 0.4558(2) 0.0358(4) Uani 1 1 d . . . H1A H -0.2091 0.4137 0.4607 0.054 Uiso 1 1 calc R . . H1B H -0.4066 0.4208 0.3525 0.054 Uiso 1 1 calc R . . H1C H -0.3378 0.4267 0.5623 0.054 Uiso 1 1 calc R . . H2 H 0.267(2) 0.7012(11) 1.220(2) 0.054(6) 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 O2 0.0257(5) 0.0232(6) 0.0207(5) -0.0025(4) 0.0124(4) -0.0027(4) O1 0.0346(6) 0.0258(6) 0.0259(6) -0.0011(4) -0.0010(4) -0.0066(5) N1 0.0189(6) 0.0187(6) 0.0198(6) -0.0012(5) 0.0078(5) -0.0029(5) C5 0.0162(6) 0.0164(7) 0.0210(7) 0.0002(5) 0.0112(5) 0.0010(5) C7 0.0246(7) 0.0153(7) 0.0261(7) 0.0008(6) 0.0113(6) 0.0008(6) C9 0.0175(7) 0.0152(7) 0.0159(6) -0.0041(5) 0.0055(5) -0.0020(5) C8 0.0198(7) 0.0149(7) 0.0193(7) 0.0006(5) 0.0098(5) 0.0011(5) C6 0.0199(7) 0.0183(7) 0.0208(7) 0.0032(5) 0.0075(5) 0.0048(5) C2 0.0218(7) 0.0239(8) 0.0197(7) -0.0017(6) 0.0070(6) -0.0032(6) C3 0.0277(8) 0.0255(8) 0.0222(7) 0.0064(6) 0.0019(6) 0.0005(6) C10 0.0245(7) 0.0219(8) 0.0230(7) 0.0019(6) 0.0106(6) 0.0034(6) C13 0.0217(7) 0.0257(8) 0.0250(7) -0.0029(6) 0.0120(6) -0.0059(6) C11 0.0228(7) 0.0260(8) 0.0275(8) -0.0007(6) 0.0067(6) 0.0078(6) C4 0.0243(7) 0.0171(7) 0.0274(8) 0.0048(6) 0.0093(6) 0.0000(6) C12 0.0166(7) 0.0316(9) 0.0312(8) -0.0071(6) 0.0110(6) -0.0005(6) C1 0.0427(9) 0.0255(9) 0.0333(9) -0.0071(7) 0.0059(7) -0.0102(7) _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 O2 C8 1.4242(15) . ? O2 H2 0.90(2) . ? O1 C2 1.3669(16) . ? O1 C1 1.4213(18) . ? N1 C9 1.3416(17) . ? N1 C13 1.3426(17) . ? C5 C8 1.5150(17) . ? C5 C6 1.3874(18) . ? C5 C4 1.3910(18) . ? C7 H7 0.9500 . ? C7 C6 1.3894(19) . ? C7 C2 1.3859(19) . ? C9 C8 1.5212(17) . ? C9 C10 1.3875(18) . ? C8 H8 1.0000 . ? C6 H6 0.9500 . ? C2 C3 1.390(2) . ? C3 H3 0.9500 . ? C3 C4 1.382(2) . ? C10 H10 0.9500 . ? C10 C11 1.3825(19) . ? C13 H13 0.9500 . ? C13 C12 1.378(2) . ? C11 H11 0.9500 . ? C11 C12 1.383(2) . ? C4 H4 0.9500 . ? C12 H12 0.9500 . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? 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 C8 O2 H2 104.5(12) . . ? C2 O1 C1 117.67(11) . . ? C9 N1 C13 117.61(11) . . ? C6 C5 C8 120.68(11) . . ? C6 C5 C4 118.15(12) . . ? C4 C5 C8 121.17(12) . . ? C6 C7 H7 120.4 . . ? C2 C7 H7 120.4 . . ? C2 C7 C6 119.18(12) . . ? N1 C9 C8 116.06(11) . . ? N1 C9 C10 122.32(12) . . ? C10 C9 C8 121.61(12) . . ? O2 C8 C5 108.84(10) . . ? O2 C8 C9 111.01(10) . . ? O2 C8 H8 108.9 . . ? C5 C8 C9 110.36(10) . . ? C5 C8 H8 108.9 . . ? C9 C8 H8 108.9 . . ? C5 C6 C7 121.82(12) . . ? C5 C6 H6 119.1 . . ? C7 C6 H6 119.1 . . ? O1 C2 C7 124.94(13) . . ? O1 C2 C3 115.37(12) . . ? C7 C2 C3 119.69(12) . . ? C2 C3 H3 119.8 . . ? C4 C3 C2 120.43(13) . . ? C4 C3 H3 119.8 . . ? C9 C10 H10 120.5 . . ? C11 C10 C9 119.09(13) . . ? C11 C10 H10 120.5 . . ? N1 C13 H13 118.2 . . ? N1 C13 C12 123.69(13) . . ? C12 C13 H13 118.2 . . ? C10 C11 H11 120.5 . . ? C10 C11 C12 119.06(13) . . ? C12 C11 H11 120.5 . . ? C5 C4 H4 119.6 . . ? C3 C4 C5 120.73(13) . . ? C3 C4 H4 119.6 . . ? C13 C12 C11 118.21(12) . . ? C13 C12 H12 120.9 . . ? C11 C12 H12 120.9 . . ? O1 C1 H1A 109.5 . . ? O1 C1 H1B 109.5 . . ? O1 C1 H1C 109.5 . . ? H1A C1 H1B 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 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 C4 178.85(13) . . . . ? N1 C9 C8 O2 -154.46(11) . . . . ? N1 C9 C8 C5 84.78(14) . . . . ? N1 C9 C10 C11 -0.2(2) . . . . ? N1 C13 C12 C11 0.4(2) . . . . ? C7 C2 C3 C4 -0.5(2) . . . . ? C9 N1 C13 C12 -1.3(2) . . . . ? C9 C10 C11 C12 -0.7(2) . . . . ? C8 C5 C6 C7 -179.92(12) . . . . ? C8 C5 C4 C3 179.58(13) . . . . ? C8 C9 C10 C11 179.17(12) . . . . ? C6 C5 C8 O2 -48.06(15) . . . . ? C6 C5 C8 C9 73.99(15) . . . . ? C6 C5 C4 C3 0.12(19) . . . . ? C6 C7 C2 O1 -179.11(13) . . . . ? C6 C7 C2 C3 0.1(2) . . . . ? C2 C7 C6 C5 0.3(2) . . . . ? C2 C3 C4 C5 0.3(2) . . . . ? C10 C9 C8 O2 26.13(17) . . . . ? C10 C9 C8 C5 -94.64(14) . . . . ? C10 C11 C12 C13 0.6(2) . . . . ? C13 N1 C9 C8 -178.25(11) . . . . ? C13 N1 C9 C10 1.16(18) . . . . ? C4 C5 C8 O2 132.49(12) . . . . ? C4 C5 C8 C9 -105.46(14) . . . . ? C4 C5 C6 C7 -0.45(19) . . . . ? C1 O1 C2 C7 -2.2(2) . . . . ? C1 O1 C2 C3 178.57(13) . . . . ? data_2m _database_code_depnum_ccdc_archive 'CCDC 847590' #TrackingRef 'CIF combined.cif' _audit_creation_date 2012-10-28 _audit_creation_method ; Olex2 1.2 (compiled 2012.05.09 svn.r2324, GUI svn.r4230) ; _chemical_name_common (1H-indol-3-yl)(pyridin-2-yl)methanol _chemical_name_systematic ; (1H-indol-3-yl)(pyridin-2-yl)methanol ; _chemical_formula_moiety 'C14 H12 N2 O' _chemical_formula_sum 'C14 H12 N2 O' _chemical_formula_weight 224.26 _chemical_melting_point 433 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' _space_group_crystal_system orthorhombic _space_group_IT_number 29 _space_group_name_H-M_alt 'P c a 21' _space_group_name_Hall 'P 2c -2ac' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, z+1/2' 3 '-x+1/2, y, z+1/2' 4 'x+1/2, -y, z' _cell_length_a 10.6147(5) _cell_length_b 11.5927(5) _cell_length_c 9.2553(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1138.90(9) _cell_formula_units_Z 4 _cell_measurement_reflns_used 2594 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 29.2356 _cell_measurement_theta_min 2.8105 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_T_max 0.993 _exptl_absorpt_correction_T_min 0.956 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.308 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 472 _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.08 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0248 _diffrn_reflns_av_unetI/netI 0.0302 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 4040 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 3.41 _diffrn_ambient_temperature 298(2) _diffrn_detector_area_resol_mean 15.9821 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -81.00 -49.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - -17.9647 -37.0000 -60.0000 32 #__ type_ start__ end____ width___ exp.time_ 2 omega -27.00 88.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 19.6053 0.0000 -120.0000 115 #__ type_ start__ end____ width___ exp.time_ 3 omega 34.00 85.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - 19.6053 179.0000 -120.0000 51 #__ type_ start__ end____ width___ exp.time_ 4 omega -90.00 -65.00 1.0000 10.0000 omega____ theta____ kappa____ phi______ frames - -17.9647 -37.0000 0.0000 25 ; _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0176210000 _diffrn_orient_matrix_UB_12 -0.0249176000 _diffrn_orient_matrix_UB_13 0.0670005000 _diffrn_orient_matrix_UB_21 -0.0412946000 _diffrn_orient_matrix_UB_22 0.0382098000 _diffrn_orient_matrix_UB_23 0.0365698000 _diffrn_orient_matrix_UB_31 -0.0495252000 _diffrn_orient_matrix_UB_32 -0.0407708000 _diffrn_orient_matrix_UB_33 -0.0065806000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 1744 _reflns_number_total 1944 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; SHELXS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.115 _refine_diff_density_min -0.127 _refine_diff_density_rms 0.031 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -1.3(17) _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 158 _refine_ls_number_reflns 1944 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0455 _refine_ls_R_factor_gt 0.0388 _refine_ls_restrained_S_all 1.060 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0592P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0944 _refine_ls_wR_factor_ref 0.1022 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.35551(15) 0.79868(13) 0.21956(16) 0.0536(4) Uani 1 1 d . . . C7 C 0.38370(17) 0.91763(15) 0.4239(2) 0.0368(4) Uani 1 1 d . . . C1 C 0.37959(19) 0.70374(15) 0.4495(2) 0.0373(4) Uani 1 1 d . . . N2 N 0.50892(17) 1.04418(13) 0.5365(2) 0.0479(4) Uani 1 1 d . . . H2 H 0.5655 1.0712 0.5938 0.057 Uiso 1 1 calc R . . N1 N 0.31093(17) 0.65860(15) 0.5557(2) 0.0531(5) Uani 1 1 d . . . C8 C 0.4763(2) 0.93076(16) 0.5239(2) 0.0434(5) Uani 1 1 d . . . H8 H 0.5124 0.8709 0.5764 0.052 Uiso 1 1 calc R . . C9 C 0.43714(18) 1.10802(16) 0.4436(2) 0.0405(5) Uani 1 1 d . . . C6 C 0.32694(18) 0.80701(16) 0.3710(2) 0.0394(5) Uani 1 1 d . . . H6 H 0.2354 0.8096 0.3841 0.047 Uiso 1 1 calc R . . C13 C 0.26984(18) 1.07646(16) 0.2703(2) 0.0459(5) Uani 1 1 d . . . H13 H 0.2138 1.0283 0.2221 0.055 Uiso 1 1 calc R . . C10 C 0.4369(2) 1.22610(17) 0.4165(3) 0.0499(5) Uani 1 1 d . . . H10 H 0.4919 1.2755 0.4644 0.060 Uiso 1 1 calc R . . C14 C 0.35494(16) 1.03175(15) 0.3708(2) 0.0366(4) Uani 1 1 d . . . C2 C 0.4969(2) 0.6596(2) 0.4146(3) 0.0618(6) Uani 1 1 d . . . H2A H 0.5448 0.6937 0.3422 0.074 Uiso 1 1 calc R . . C12 C 0.2707(2) 1.19361(19) 0.2441(3) 0.0561(6) Uani 1 1 d . . . H12 H 0.2152 1.2242 0.1766 0.067 Uiso 1 1 calc R . . C11 C 0.3528(2) 1.26678(18) 0.3165(3) 0.0564(6) Uani 1 1 d . . . H11 H 0.3507 1.3454 0.2966 0.068 Uiso 1 1 calc R . . C5 C 0.3580(3) 0.5665(2) 0.6250(3) 0.0722(8) Uani 1 1 d . . . H5 H 0.3106 0.5345 0.6993 0.087 Uiso 1 1 calc R . . C4 C 0.4716(3) 0.5169(2) 0.5931(3) 0.0748(8) Uani 1 1 d . . . H4 H 0.4996 0.4519 0.6424 0.090 Uiso 1 1 calc R . . C3 C 0.5420(3) 0.5653(2) 0.4876(3) 0.0798(9) Uani 1 1 d . . . H3 H 0.6205 0.5349 0.4646 0.096 Uiso 1 1 calc R . . H1 H 0.302(3) 0.749(2) 0.176(4) 0.100(11) 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 O1 0.0695(10) 0.0599(10) 0.0315(8) -0.0004(8) -0.0017(7) -0.0259(8) C7 0.0380(9) 0.0396(10) 0.0327(10) 0.0006(9) 0.0000(9) -0.0033(8) C1 0.0427(10) 0.0366(9) 0.0326(10) -0.0061(9) 0.0039(8) -0.0063(9) N2 0.0532(10) 0.0461(9) 0.0443(10) -0.0045(10) -0.0171(9) -0.0064(8) N1 0.0590(10) 0.0502(10) 0.0501(12) 0.0109(9) 0.0083(10) -0.0027(8) C8 0.0497(12) 0.0407(10) 0.0398(12) 0.0039(10) -0.0088(10) -0.0041(9) C9 0.0424(11) 0.0425(9) 0.0367(10) -0.0028(10) 0.0042(9) 0.0001(9) C6 0.0388(10) 0.0461(11) 0.0333(11) 0.0011(9) -0.0009(9) -0.0102(8) C13 0.0423(10) 0.0547(11) 0.0408(12) 0.0011(11) -0.0031(10) 0.0050(10) C10 0.0561(12) 0.0410(10) 0.0527(13) -0.0044(11) 0.0062(11) -0.0061(9) C14 0.0343(9) 0.0440(10) 0.0317(10) -0.0011(9) 0.0047(8) -0.0005(8) C2 0.0621(15) 0.0734(14) 0.0497(14) -0.0020(12) 0.0094(12) 0.0128(13) C12 0.0562(13) 0.0610(13) 0.0512(14) 0.0071(11) -0.0029(12) 0.0168(11) C11 0.0682(14) 0.0417(11) 0.0592(16) 0.0070(12) 0.0131(12) 0.0101(11) C5 0.096(2) 0.0561(15) 0.0648(18) 0.0205(13) 0.0030(15) -0.0083(16) C4 0.117(2) 0.0462(13) 0.0607(17) -0.0010(13) -0.0142(17) 0.0206(16) C3 0.0883(19) 0.0854(19) 0.0655(18) -0.0164(16) -0.0074(17) 0.0461(17) _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 C6 1.437(2) . ? O1 H1 0.91(3) . ? C7 C8 1.359(3) . ? C7 C6 1.499(3) . ? C7 C14 1.444(3) . ? C1 N1 1.331(3) . ? C1 C6 1.508(3) . ? C1 C2 1.385(3) . ? N2 H2 0.8600 . ? N2 C8 1.365(2) . ? N2 C9 1.367(3) . ? N1 C5 1.342(3) . ? C8 H8 0.9300 . ? C9 C10 1.392(2) . ? C9 C14 1.413(3) . ? C6 H6 0.9800 . ? C13 H13 0.9300 . ? C13 C14 1.396(3) . ? C13 C12 1.380(3) . ? C10 H10 0.9300 . ? C10 C11 1.370(3) . ? C2 H2A 0.9300 . ? C2 C3 1.370(4) . ? C12 H12 0.9300 . ? C12 C11 1.388(3) . ? C11 H11 0.9300 . ? C5 H5 0.9300 . ? C5 C4 1.368(4) . ? C4 H4 0.9300 . ? C4 C3 1.351(4) . ? C3 H3 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 C6 O1 H1 110(2) . . ? C8 C7 C6 127.51(17) . . ? C8 C7 C14 106.38(16) . . ? C14 C7 C6 126.02(17) . . ? N1 C1 C6 117.71(18) . . ? N1 C1 C2 121.29(19) . . ? C2 C1 C6 120.98(19) . . ? C8 N2 H2 125.5 . . ? C8 N2 C9 109.05(16) . . ? C9 N2 H2 125.5 . . ? C1 N1 C5 117.5(2) . . ? C7 C8 N2 110.47(17) . . ? C7 C8 H8 124.8 . . ? N2 C8 H8 124.8 . . ? N2 C9 C10 130.31(19) . . ? N2 C9 C14 107.78(16) . . ? C10 C9 C14 121.91(19) . . ? O1 C6 C7 106.91(16) . . ? O1 C6 C1 109.77(17) . . ? O1 C6 H6 109.4 . . ? C7 C6 C1 111.90(16) . . ? C7 C6 H6 109.4 . . ? C1 C6 H6 109.4 . . ? C14 C13 H13 120.7 . . ? C12 C13 H13 120.7 . . ? C12 C13 C14 118.55(19) . . ? C9 C10 H10 121.3 . . ? C11 C10 C9 117.5(2) . . ? C11 C10 H10 121.3 . . ? C9 C14 C7 106.31(16) . . ? C13 C14 C7 134.70(17) . . ? C13 C14 C9 119.00(17) . . ? C1 C2 H2A 120.2 . . ? C3 C2 C1 119.6(2) . . ? C3 C2 H2A 120.2 . . ? C13 C12 H12 119.3 . . ? C13 C12 C11 121.4(2) . . ? C11 C12 H12 119.3 . . ? C10 C11 C12 121.65(19) . . ? C10 C11 H11 119.2 . . ? C12 C11 H11 119.2 . . ? N1 C5 H5 118.0 . . ? N1 C5 C4 124.0(3) . . ? C4 C5 H5 118.0 . . ? C5 C4 H4 121.0 . . ? C3 C4 C5 118.0(2) . . ? C3 C4 H4 121.0 . . ? C2 C3 H3 120.2 . . ? C4 C3 C2 119.6(3) . . ? C4 C3 H3 120.2 . . ? 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 C1 N1 C5 C4 0.0(4) . . . . ? C1 C2 C3 C4 -0.3(4) . . . . ? N2 C9 C10 C11 -179.6(2) . . . . ? N2 C9 C14 C7 -1.1(2) . . . . ? N2 C9 C14 C13 179.16(19) . . . . ? N1 C1 C6 O1 -141.50(19) . . . . ? N1 C1 C6 C7 100.0(2) . . . . ? N1 C1 C2 C3 2.0(4) . . . . ? N1 C5 C4 C3 1.6(5) . . . . ? C8 C7 C6 O1 -116.8(2) . . . . ? C8 C7 C6 C1 3.4(3) . . . . ? C8 C7 C14 C9 1.1(2) . . . . ? C8 C7 C14 C13 -179.2(2) . . . . ? C8 N2 C9 C10 -179.2(2) . . . . ? C8 N2 C9 C14 0.7(2) . . . . ? C9 N2 C8 C7 0.0(2) . . . . ? C9 C10 C11 C12 -0.2(3) . . . . ? C6 C7 C8 N2 175.91(19) . . . . ? C6 C7 C14 C9 -175.56(17) . . . . ? C6 C7 C14 C13 4.1(3) . . . . ? C6 C1 N1 C5 179.8(2) . . . . ? C6 C1 C2 C3 -179.7(2) . . . . ? C13 C12 C11 C10 0.3(4) . . . . ? C10 C9 C14 C7 178.76(18) . . . . ? C10 C9 C14 C13 -0.9(3) . . . . ? C14 C7 C8 N2 -0.7(2) . . . . ? C14 C7 C6 O1 59.2(2) . . . . ? C14 C7 C6 C1 179.40(16) . . . . ? C14 C9 C10 C11 0.5(3) . . . . ? C14 C13 C12 C11 -0.8(3) . . . . ? C2 C1 N1 C5 -1.9(3) . . . . ? C2 C1 C6 O1 40.2(2) . . . . ? C2 C1 C6 C7 -78.3(2) . . . . ? C12 C13 C14 C7 -178.6(2) . . . . ? C12 C13 C14 C9 1.0(3) . . . . ? C5 C4 C3 C2 -1.4(4) . . . . ? data_6a _database_code_depnum_ccdc_archive 'CCDC 847592' #TrackingRef 'CIF combined.cif' _audit_creation_date 2012-10-28 _audit_creation_method ; Olex2 1.2 (compiled 2012.05.09 svn.r2324, GUI svn.r4230) ; _chemical_name_common 4,4'-(phenylmethylene)bis(methoxybenzene) _chemical_name_systematic ; 4,4'-(phenylmethylene)bis(methoxybenzene) ; _chemical_formula_moiety 'C21 H20 O2' _chemical_formula_sum 'C21 H20 O2' _chemical_formula_weight 304.37 _chemical_melting_point 352 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' _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_H-M_alt 'P 21 21 21' _space_group_name_Hall 'P 2ac 2ab' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, -y, z+1/2' 3 'x+1/2, -y+1/2, -z' 4 '-x, y+1/2, -z+1/2' _cell_length_a 5.9087(2) _cell_length_b 12.7700(5) _cell_length_c 21.8373(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1647.71(10) _cell_formula_units_Z 4 _cell_measurement_reflns_used 3634 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 29.2097 _cell_measurement_theta_min 2.7927 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_T_max 0.971 _exptl_absorpt_correction_T_min 0.964 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.227 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 648 _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.35 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0134 _diffrn_reflns_av_unetI/netI 0.0236 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_number 4917 _diffrn_reflns_theta_full 24.98 _diffrn_reflns_theta_max 24.98 _diffrn_reflns_theta_min 3.19 _diffrn_ambient_temperature 298(2) _diffrn_detector_area_resol_mean 15.9821 _diffrn_measured_fraction_theta_full 0.986 _diffrn_measured_fraction_theta_max 0.986 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -92.00 -67.00 1.0000 35.0000 omega____ theta____ kappa____ phi______ frames - -17.4960 167.0000 -113.0000 25 #__ type_ start__ end____ width___ exp.time_ 2 omega -5.00 92.00 1.0000 35.0000 omega____ theta____ kappa____ phi______ frames - 19.2928 37.0000 0.0000 97 #__ type_ start__ end____ width___ exp.time_ 3 omega -2.00 48.00 1.0000 35.0000 omega____ theta____ kappa____ phi______ frames - 19.2928 37.0000 90.0000 50 ; _diffrn_measurement_device_type 'Xcalibur, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0152232000 _diffrn_orient_matrix_UB_12 0.0305054000 _diffrn_orient_matrix_UB_13 0.0268398000 _diffrn_orient_matrix_UB_21 0.0328676000 _diffrn_orient_matrix_UB_22 0.0455225000 _diffrn_orient_matrix_UB_23 -0.0163277000 _diffrn_orient_matrix_UB_31 -0.1144644000 _diffrn_orient_matrix_UB_32 0.0090390000 _diffrn_orient_matrix_UB_33 -0.0082414000 _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 2506 _reflns_number_total 2795 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; SHELXS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.103 _refine_diff_density_min -0.127 _refine_diff_density_rms 0.028 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.5(14) _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 210 _refine_ls_number_reflns 2795 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0407 _refine_ls_R_factor_gt 0.0341 _refine_ls_restrained_S_all 1.066 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0344P)^2^+0.2007P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0757 _refine_ls_wR_factor_ref 0.0807 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 C7 C 0.3642(3) 0.57432(12) 0.68913(7) 0.0346(4) Uani 1 1 d . . . H7 H 0.4995 0.5853 0.7143 0.041 Uiso 1 1 calc R . . C17 C 0.4886(3) 0.28382(13) 0.59303(7) 0.0384(4) Uani 1 1 d . . . C3 C 0.1753(3) 0.68615(14) 0.60635(7) 0.0418(4) Uani 1 1 d . . . H3 H 0.0530 0.6403 0.6067 0.050 Uiso 1 1 calc R . . C8 C 0.1664(3) 0.56734(13) 0.73437(6) 0.0350(4) Uani 1 1 d . . . O1 O 0.3666(2) 0.92499(10) 0.52789(6) 0.0618(4) Uani 1 1 d . . . C1 C 0.3516(3) 0.83914(13) 0.56522(7) 0.0406(4) Uani 1 1 d . . . O2 O 0.5107(2) 0.19199(9) 0.56112(6) 0.0523(3) Uani 1 1 d . . . C16 C 0.2862(3) 0.33696(14) 0.58425(7) 0.0412(4) Uani 1 1 d . . . H16 H 0.1776 0.3102 0.5577 0.049 Uiso 1 1 calc R . . C2 C 0.1730(3) 0.77022(14) 0.56601(8) 0.0430(4) Uani 1 1 d . . . H2 H 0.0511 0.7798 0.5397 0.052 Uiso 1 1 calc R . . C19 C 0.6044(3) 0.41810(14) 0.66253(8) 0.0419(4) Uani 1 1 d . . . H19 H 0.7137 0.4450 0.6888 0.050 Uiso 1 1 calc R . . C4 C 0.3531(3) 0.66831(12) 0.64601(7) 0.0337(4) Uani 1 1 d . . . C14 C 0.4052(3) 0.47235(13) 0.65476(7) 0.0328(4) Uani 1 1 d . . . C15 C 0.2464(3) 0.42922(13) 0.61485(8) 0.0413(4) Uani 1 1 d . . . H15 H 0.1097 0.4638 0.6088 0.050 Uiso 1 1 calc R . . C13 C 0.1204(3) 0.47385(15) 0.76435(8) 0.0463(4) Uani 1 1 d . . . H13 H 0.2044 0.4145 0.7548 0.056 Uiso 1 1 calc R . . C18 C 0.6474(3) 0.32430(14) 0.63233(8) 0.0451(4) Uani 1 1 d . . . H18 H 0.7832 0.2892 0.6387 0.054 Uiso 1 1 calc R . . C6 C 0.5310(3) 0.82292(15) 0.60453(9) 0.0514(5) Uani 1 1 d . . . H6 H 0.6530 0.8689 0.6043 0.062 Uiso 1 1 calc R . . C11 C -0.1736(3) 0.55412(17) 0.82316(8) 0.0553(5) Uani 1 1 d . . . H11 H -0.2868 0.5497 0.8526 0.066 Uiso 1 1 calc R . . C9 C 0.0381(3) 0.65382(14) 0.75039(8) 0.0451(4) Uani 1 1 d . . . H9 H 0.0656 0.7176 0.7313 0.054 Uiso 1 1 calc R . . C5 C 0.5303(3) 0.73884(14) 0.64419(8) 0.0450(4) Uani 1 1 d . . . H5 H 0.6525 0.7294 0.6704 0.054 Uiso 1 1 calc R . . C10 C -0.1298(3) 0.64726(17) 0.79421(8) 0.0537(5) Uani 1 1 d . . . H10 H -0.2139 0.7064 0.8042 0.064 Uiso 1 1 calc R . . C12 C -0.0477(3) 0.46750(16) 0.80802(8) 0.0551(5) Uani 1 1 d . . . H12 H -0.0760 0.4040 0.8274 0.066 Uiso 1 1 calc R . . C20 C 0.7051(4) 0.12975(15) 0.57361(10) 0.0617(6) Uani 1 1 d . . . H20A H 0.6966 0.0658 0.5506 0.093 Uiso 1 1 calc R . . H20B H 0.7108 0.1140 0.6166 0.093 Uiso 1 1 calc R . . H20C H 0.8388 0.1675 0.5620 0.093 Uiso 1 1 calc R . . C21 C 0.1741(4) 0.95449(18) 0.49374(10) 0.0754(7) Uani 1 1 d . . . H21A H 0.1396 0.9008 0.4644 0.113 Uiso 1 1 calc R . . H21B H 0.2040 1.0191 0.4727 0.113 Uiso 1 1 calc R . . H21C H 0.0477 0.9636 0.5209 0.113 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 C7 0.0348(8) 0.0388(9) 0.0301(8) -0.0015(7) -0.0071(7) -0.0021(7) C17 0.0454(10) 0.0359(10) 0.0339(8) 0.0039(7) 0.0076(8) -0.0007(8) C3 0.0417(9) 0.0414(10) 0.0423(9) 0.0002(8) -0.0084(8) -0.0051(8) C8 0.0402(9) 0.0401(10) 0.0245(7) -0.0025(6) -0.0042(7) -0.0012(8) O1 0.0732(9) 0.0515(9) 0.0606(8) 0.0210(7) -0.0014(8) 0.0022(7) C1 0.0499(10) 0.0374(10) 0.0346(8) 0.0022(7) 0.0045(8) 0.0047(9) O2 0.0585(8) 0.0431(7) 0.0553(7) -0.0084(6) 0.0011(7) 0.0047(6) C16 0.0404(9) 0.0443(11) 0.0390(9) -0.0026(7) -0.0075(8) -0.0033(8) C2 0.0489(10) 0.0461(10) 0.0339(8) -0.0013(7) -0.0112(8) 0.0044(9) C19 0.0360(9) 0.0475(11) 0.0421(9) -0.0012(8) -0.0080(8) 0.0023(8) C4 0.0347(8) 0.0372(9) 0.0292(8) -0.0030(7) 0.0000(7) -0.0004(7) C14 0.0320(8) 0.0378(9) 0.0286(8) 0.0042(7) 0.0005(7) 0.0002(7) C15 0.0352(9) 0.0434(10) 0.0453(10) -0.0015(8) -0.0059(8) 0.0035(8) C13 0.0583(11) 0.0442(11) 0.0362(9) 0.0020(8) 0.0071(9) 0.0039(9) C18 0.0377(9) 0.0465(11) 0.0510(10) 0.0008(8) -0.0029(9) 0.0095(9) C6 0.0430(10) 0.0485(11) 0.0628(12) 0.0095(9) -0.0027(10) -0.0095(9) C11 0.0540(11) 0.0776(15) 0.0342(9) -0.0043(9) 0.0108(10) -0.0037(11) C9 0.0540(11) 0.0455(11) 0.0357(8) -0.0012(8) 0.0009(9) 0.0026(9) C5 0.0363(9) 0.0483(11) 0.0503(10) 0.0049(9) -0.0091(9) -0.0040(8) C10 0.0575(12) 0.0645(14) 0.0390(9) -0.0087(9) 0.0045(10) 0.0128(10) C12 0.0694(13) 0.0557(12) 0.0401(10) 0.0060(9) 0.0105(10) -0.0095(10) C20 0.0616(12) 0.0461(12) 0.0775(14) -0.0050(10) 0.0067(13) 0.0122(10) C21 0.0907(17) 0.0702(15) 0.0654(13) 0.0279(11) -0.0104(14) 0.0141(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 C7 H7 0.9800 . ? C7 C8 1.533(2) . ? C7 C4 1.527(2) . ? C7 C14 1.522(2) . ? C17 O2 1.3703(19) . ? C17 C16 1.388(2) . ? C17 C18 1.373(2) . ? C3 H3 0.9300 . ? C3 C2 1.389(2) . ? C3 C4 1.381(2) . ? C8 C13 1.389(2) . ? C8 C9 1.384(2) . ? O1 C1 1.369(2) . ? O1 C21 1.411(2) . ? C1 C2 1.375(2) . ? C1 C6 1.379(2) . ? O2 C20 1.423(2) . ? C16 H16 0.9300 . ? C16 C15 1.375(2) . ? C2 H2 0.9300 . ? C19 H19 0.9300 . ? C19 C14 1.376(2) . ? C19 C18 1.391(2) . ? C4 C5 1.381(2) . ? C14 C15 1.394(2) . ? C15 H15 0.9300 . ? C13 H13 0.9300 . ? C13 C12 1.379(2) . ? C18 H18 0.9300 . ? C6 H6 0.9300 . ? C6 C5 1.379(2) . ? C11 H11 0.9300 . ? C11 C10 1.372(3) . ? C11 C12 1.373(3) . ? C9 H9 0.9300 . ? C9 C10 1.381(3) . ? C5 H5 0.9300 . ? C10 H10 0.9300 . ? C12 H12 0.9300 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? 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 C8 C7 H7 105.6 . . ? C4 C7 H7 105.6 . . ? C4 C7 C8 114.23(13) . . ? C14 C7 H7 105.6 . . ? C14 C7 C8 112.93(13) . . ? C14 C7 C4 112.03(12) . . ? O2 C17 C16 115.48(16) . . ? O2 C17 C18 125.09(16) . . ? C18 C17 C16 119.42(16) . . ? C2 C3 H3 118.9 . . ? C4 C3 H3 118.9 . . ? C4 C3 C2 122.21(16) . . ? C13 C8 C7 120.22(15) . . ? C9 C8 C7 122.28(14) . . ? C9 C8 C13 117.34(15) . . ? C1 O1 C21 118.45(15) . . ? O1 C1 C2 124.73(16) . . ? O1 C1 C6 116.19(16) . . ? C2 C1 C6 119.08(15) . . ? C17 O2 C20 117.23(15) . . ? C17 C16 H16 120.0 . . ? C15 C16 C17 119.94(16) . . ? C15 C16 H16 120.0 . . ? C3 C2 H2 120.2 . . ? C1 C2 C3 119.69(16) . . ? C1 C2 H2 120.2 . . ? C14 C19 H19 118.9 . . ? C14 C19 C18 122.11(16) . . ? C18 C19 H19 118.9 . . ? C3 C4 C7 123.31(14) . . ? C3 C4 C5 116.81(15) . . ? C5 C4 C7 119.86(14) . . ? C19 C14 C7 120.40(14) . . ? C19 C14 C15 117.00(15) . . ? C15 C14 C7 122.60(14) . . ? C16 C15 C14 121.81(15) . . ? C16 C15 H15 119.1 . . ? C14 C15 H15 119.1 . . ? C8 C13 H13 119.4 . . ? C12 C13 C8 121.18(17) . . ? C12 C13 H13 119.4 . . ? C17 C18 C19 119.72(16) . . ? C17 C18 H18 120.1 . . ? C19 C18 H18 120.1 . . ? C1 C6 H6 119.8 . . ? C1 C6 C5 120.35(16) . . ? C5 C6 H6 119.8 . . ? C10 C11 H11 120.5 . . ? C10 C11 C12 119.04(17) . . ? C12 C11 H11 120.5 . . ? C8 C9 H9 119.3 . . ? C10 C9 C8 121.35(17) . . ? C10 C9 H9 119.3 . . ? C4 C5 H5 119.1 . . ? C6 C5 C4 121.86(16) . . ? C6 C5 H5 119.1 . . ? C11 C10 C9 120.49(18) . . ? C11 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? C13 C12 H12 119.7 . . ? C11 C12 C13 120.61(18) . . ? C11 C12 H12 119.7 . . ? O2 C20 H20A 109.5 . . ? O2 C20 H20B 109.5 . . ? O2 C20 H20C 109.5 . . ? H20A C20 H20B 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? O1 C21 H21A 109.5 . . ? O1 C21 H21B 109.5 . . ? O1 C21 H21C 109.5 . . ? H21A C21 H21B 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 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 C7 C8 C13 C12 175.94(15) . . . . ? C7 C8 C9 C10 -175.73(16) . . . . ? C7 C4 C5 C6 177.83(16) . . . . ? C7 C14 C15 C16 -179.91(15) . . . . ? C17 C16 C15 C14 0.4(2) . . . . ? C3 C4 C5 C6 -0.3(3) . . . . ? C8 C7 C4 C3 -59.07(19) . . . . ? C8 C7 C4 C5 122.92(16) . . . . ? C8 C7 C14 C19 -115.82(16) . . . . ? C8 C7 C14 C15 63.74(19) . . . . ? C8 C13 C12 C11 -0.3(3) . . . . ? C8 C9 C10 C11 0.1(3) . . . . ? O1 C1 C2 C3 -179.41(16) . . . . ? O1 C1 C6 C5 179.54(16) . . . . ? C1 C6 C5 C4 0.2(3) . . . . ? O2 C17 C16 C15 179.14(15) . . . . ? O2 C17 C18 C19 -179.48(15) . . . . ? C16 C17 O2 C20 -173.68(15) . . . . ? C16 C17 C18 C19 -0.4(3) . . . . ? C2 C3 C4 C7 -177.64(15) . . . . ? C2 C3 C4 C5 0.4(2) . . . . ? C2 C1 C6 C5 -0.2(3) . . . . ? C19 C14 C15 C16 -0.3(2) . . . . ? C4 C7 C8 C13 162.54(14) . . . . ? C4 C7 C8 C9 -22.2(2) . . . . ? C4 C7 C14 C19 113.50(16) . . . . ? C4 C7 C14 C15 -66.94(19) . . . . ? C4 C3 C2 C1 -0.4(3) . . . . ? C14 C7 C8 C13 33.0(2) . . . . ? C14 C7 C8 C9 -151.77(15) . . . . ? C14 C7 C4 C3 70.94(19) . . . . ? C14 C7 C4 C5 -107.07(17) . . . . ? C14 C19 C18 C17 0.4(3) . . . . ? C13 C8 C9 C10 -0.3(2) . . . . ? C18 C17 O2 C20 5.5(2) . . . . ? C18 C17 C16 C15 -0.1(2) . . . . ? C18 C19 C14 C7 179.49(15) . . . . ? C18 C19 C14 C15 -0.1(2) . . . . ? C6 C1 C2 C3 0.3(3) . . . . ? C9 C8 C13 C12 0.5(3) . . . . ? C10 C11 C12 C13 0.0(3) . . . . ? C12 C11 C10 C9 0.1(3) . . . . ? C21 O1 C1 C2 9.4(3) . . . . ? C21 O1 C1 C6 -170.35(18) . . . . ? #END=====