Electronic Supplementary Material for CrystEngComm This Journal is (c) The Royal Society of Chemistry 2006 data_global _journal_coden_Cambridge 1350 loop_ _publ_author_name 'J. Scheffer' ; Brian O'Patrick ; 'Wujiong Xia' 'Chao Yang' _publ_contact_author_name 'John Scheffer' _publ_contact_author_address ; Department of Chemistry University of British Columbia 2036 Main Mall Vancouver British Columbia V6T 1Z3 CANADA ; _publ_contact_author_email SCHEFFER@CHEM.UBC.CA _publ_requested_journal 'Cryst Eng. Comm.' _publ_section_title ; Engineering Acyclic Alky Aryl Ketones for Enantioselective Norrish/Yang Type II Photochemistry in the Crystalline State ; # Attachment 'CrystEngComm-CIF.cif' data_hklf4 _database_code_depnum_ccdc_archive 'CCDC 297457' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H27 N O3' _chemical_formula_weight 341.44 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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 212121' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 6.121(2) _cell_length_b 7.073(3) _cell_length_c 45.30(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1961.2(14) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1741 _cell_measurement_theta_min 2.74 _cell_measurement_theta_max 21.03 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.156 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2412 _diffrn_reflns_av_R_equivalents 0.0300 _diffrn_reflns_av_sigmaI/netI 0.0661 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -47 _diffrn_reflns_limit_l_max 48 _diffrn_reflns_theta_min 2.70 _diffrn_reflns_theta_max 22.54 _reflns_number_total 2412 _reflns_number_gt 1865 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.044(15) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -5(7) _refine_ls_number_reflns 2412 _refine_ls_number_parameters 231 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1562 _refine_ls_R_factor_gt 0.1381 _refine_ls_wR_factor_ref 0.3664 _refine_ls_wR_factor_gt 0.3567 _refine_ls_goodness_of_fit_ref 1.426 _refine_ls_restrained_S_all 1.426 _refine_ls_shift/su_max 0.309 _refine_ls_shift/su_mean 0.039 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 0.7242(16) 0.9993(14) 0.3567(2) 0.036(2) Uani 1 1 d . . . C2 C 0.9350(18) 0.9319(15) 0.3626(2) 0.047(3) Uani 1 1 d . . . H2 H 1.0321 0.9052 0.3468 0.056 Uiso 1 1 calc R . . C3 C 1.0038(16) 0.9035(15) 0.3924(2) 0.039(2) Uani 1 1 d . . . H3 H 1.1491 0.8623 0.3960 0.047 Uiso 1 1 calc R . . C4 C 0.8707(14) 0.9329(12) 0.41551(18) 0.026(2) Uani 1 1 d . . . C5 C 0.6467(15) 0.9991(12) 0.4091(2) 0.033(2) Uani 1 1 d . . . H5 H 0.5423 1.0161 0.4244 0.039 Uiso 1 1 calc R . . C6 C 0.5962(15) 1.0348(14) 0.3804(2) 0.035(2) Uani 1 1 d . . . H6 H 0.4575 1.0901 0.3767 0.042 Uiso 1 1 calc R . . C7 C 0.9419(15) 0.8983(13) 0.4460(2) 0.036(3) Uani 1 1 d . . . C8 C 0.645(2) 1.0323(18) 0.3268(2) 0.060(3) Uani 1 1 d . . . C9 C 0.7684(18) 0.9673(18) 0.2987(3) 0.056(3) Uani 1 1 d . . . H9 H 0.9066 0.8994 0.3038 0.067 Uiso 1 1 calc R . . C10 C 0.816(3) 1.158(4) 0.2801(3) 0.131(9) Uani 1 1 d . . . H10A H 0.8790 1.1241 0.2607 0.157 Uiso 1 1 calc R . . H10B H 0.6772 1.2259 0.2767 0.157 Uiso 1 1 calc R . . C11 C 0.974(5) 1.287(5) 0.2965(5) 0.226(18) Uani 1 1 d . . . H11A H 0.9438 1.2807 0.3177 0.340 Uiso 1 1 calc R . . H11B H 0.9549 1.4170 0.2896 0.340 Uiso 1 1 calc R . . H11C H 1.1241 1.2457 0.2927 0.340 Uiso 1 1 calc R . . C12 C 0.603(3) 0.833(3) 0.2799(3) 0.100(6) Uani 1 1 d . . . H12A H 0.4735 0.9073 0.2736 0.120 Uiso 1 1 calc R . . H12B H 0.6774 0.7859 0.2619 0.120 Uiso 1 1 calc R . . C13 C 0.536(5) 0.681(3) 0.2972(4) 0.149(10) Uani 1 1 d . . . H13A H 0.6365 0.6663 0.3139 0.223 Uiso 1 1 calc R . . H13B H 0.5366 0.5652 0.2854 0.223 Uiso 1 1 calc R . . H13C H 0.3880 0.7044 0.3047 0.223 Uiso 1 1 calc R . . C14 C 0.3176(12) 1.4707(14) 0.4317(2) 0.031(2) Uani 1 1 d . . . C15 C 0.1283(16) 1.4036(14) 0.4184(2) 0.041(3) Uani 1 1 d . . . H15 H 0.0120 1.3589 0.4304 0.049 Uiso 1 1 calc R . . C16 C 0.1055(16) 1.4005(15) 0.3882(2) 0.043(3) Uani 1 1 d . . . H16 H -0.0289 1.3603 0.3798 0.052 Uiso 1 1 calc R . . C17 C 0.2730(18) 1.4543(15) 0.3700(2) 0.047(3) Uani 1 1 d . . . H17 H 0.2604 1.4435 0.3492 0.057 Uiso 1 1 calc R . . C18 C 0.4646(18) 1.5262(13) 0.3831(2) 0.042(3) Uani 1 1 d . . . H18 H 0.5776 1.5749 0.3709 0.051 Uiso 1 1 calc R . . C19 C 0.4904(14) 1.5269(13) 0.4129(2) 0.032(2) Uani 1 1 d . . . H19 H 0.6258 1.5655 0.4212 0.039 Uiso 1 1 calc R . . C20 C 0.3467(14) 1.4738(13) 0.4651(2) 0.034(2) Uani 1 1 d . . . H20 H 0.2032 1.4383 0.4741 0.041 Uiso 1 1 calc R . . C21 C 0.5226(16) 1.3264(15) 0.4765(2) 0.045(3) Uani 1 1 d . . . H21A H 0.5277 1.3294 0.4981 0.067 Uiso 1 1 calc R . . H21B H 0.6665 1.3595 0.4686 0.067 Uiso 1 1 calc R . . H21C H 0.4823 1.1991 0.4699 0.067 Uiso 1 1 calc R . . N1 N 0.4012(12) 1.6672(11) 0.47554(18) 0.035(2) Uani 1 1 d . . . H1A H 0.3124 1.7525 0.4665 0.052 Uiso 1 1 calc R . . H1B H 0.5429 1.6937 0.4711 0.052 Uiso 1 1 calc R . . H1C H 0.3816 1.6738 0.4954 0.052 Uiso 1 1 calc R . . O1 O 1.1399(10) 0.9360(9) 0.45179(15) 0.0410(19) Uani 1 1 d . . . O2 O 0.8155(9) 0.8287(11) 0.46488(16) 0.044(2) Uani 1 1 d . . . O3 O 0.467(2) 1.1183(18) 0.32322(19) 0.108(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.051(6) 0.015(5) 0.040(6) 0.009(4) 0.001(5) -0.001(4) C2 0.065(7) 0.030(6) 0.045(6) 0.009(5) 0.021(5) 0.016(6) C3 0.034(5) 0.039(6) 0.045(6) 0.004(5) 0.002(5) 0.003(5) C4 0.033(5) 0.013(4) 0.031(5) -0.007(4) 0.003(4) -0.005(4) C5 0.042(5) 0.012(4) 0.044(6) -0.006(4) 0.001(4) -0.012(4) C6 0.035(5) 0.024(5) 0.044(6) 0.004(4) -0.008(4) 0.000(4) C7 0.032(5) 0.014(5) 0.063(7) 0.001(5) 0.017(5) 0.010(4) C8 0.082(9) 0.048(8) 0.049(7) 0.007(6) -0.002(7) -0.017(8) C9 0.047(6) 0.051(8) 0.069(8) -0.005(7) 0.007(6) -0.016(6) C10 0.127(14) 0.22(3) 0.048(9) 0.030(12) -0.013(9) -0.052(16) C11 0.21(3) 0.32(4) 0.15(2) 0.00(2) -0.022(19) -0.22(3) C12 0.115(13) 0.123(16) 0.062(10) 0.000(10) -0.003(9) 0.009(12) C13 0.26(3) 0.122(17) 0.066(11) 0.004(12) -0.007(15) 0.02(2) C14 0.012(4) 0.030(6) 0.051(6) 0.005(5) 0.009(4) 0.001(4) C15 0.036(5) 0.022(5) 0.065(7) -0.001(5) 0.002(5) -0.008(5) C16 0.033(5) 0.036(6) 0.061(7) -0.005(5) -0.012(5) -0.003(5) C17 0.065(7) 0.028(6) 0.050(6) -0.005(5) -0.006(5) -0.019(6) C18 0.067(7) 0.012(5) 0.048(6) -0.002(5) 0.012(5) 0.004(5) C19 0.023(4) 0.019(5) 0.056(6) -0.005(5) -0.006(4) -0.002(4) C20 0.020(4) 0.021(5) 0.062(6) 0.005(5) 0.013(4) 0.006(4) C21 0.033(5) 0.035(6) 0.067(7) 0.004(6) -0.016(5) 0.008(5) N1 0.022(4) 0.035(5) 0.047(5) -0.002(4) -0.003(3) 0.011(4) O1 0.027(4) 0.033(4) 0.063(4) 0.014(4) 0.002(3) -0.001(3) O2 0.019(3) 0.047(5) 0.065(5) 0.010(4) 0.000(3) -0.013(3) O3 0.150(10) 0.124(10) 0.048(5) 0.010(6) -0.019(6) 0.072(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.353(13) . ? C1 C2 1.401(15) . ? C1 C8 1.460(15) . ? C2 C3 1.428(15) . ? C2 H2 0.9500 . ? C3 C4 1.343(13) . ? C3 H3 0.9500 . ? C4 C7 1.471(14) . ? C4 C5 1.478(13) . ? C5 C6 1.358(13) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 O2 1.252(11) . ? C7 O1 1.268(12) . ? C8 O3 1.257(16) . ? C8 C9 1.548(17) . ? C9 C10 1.62(3) . ? C9 C12 1.63(2) . ? C9 H9 1.0000 . ? C10 C11 1.52(3) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 C13 1.39(3) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 C15 1.391(13) . ? C14 C19 1.416(13) . ? C14 C20 1.521(14) . ? C15 C16 1.378(15) . ? C15 H15 0.9500 . ? C16 C17 1.368(15) . ? C16 H16 0.9500 . ? C17 C18 1.409(15) . ? C17 H17 0.9500 . ? C18 C19 1.359(14) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? C20 N1 1.485(12) . ? C20 C21 1.586(13) . ? C20 H20 1.0000 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? N1 H1A 0.9100 . ? N1 H1B 0.9100 . ? N1 H1C 0.9100 . ? 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 C1 C2 116.4(9) . . ? C6 C1 C8 121.0(10) . . ? C2 C1 C8 122.5(10) . . ? C1 C2 C3 119.9(9) . . ? C1 C2 H2 120.0 . . ? C3 C2 H2 120.0 . . ? C4 C3 C2 122.4(10) . . ? C4 C3 H3 118.8 . . ? C2 C3 H3 118.8 . . ? C3 C4 C7 121.8(8) . . ? C3 C4 C5 117.3(8) . . ? C7 C4 C5 120.9(7) . . ? C6 C5 C4 117.3(8) . . ? C6 C5 H5 121.4 . . ? C4 C5 H5 121.4 . . ? C1 C6 C5 126.4(9) . . ? C1 C6 H6 116.8 . . ? C5 C6 H6 116.8 . . ? O2 C7 O1 122.2(10) . . ? O2 C7 C4 121.5(9) . . ? O1 C7 C4 116.2(8) . . ? O3 C8 C1 119.0(11) . . ? O3 C8 C9 117.6(11) . . ? C1 C8 C9 123.5(12) . . ? C8 C9 C10 105.6(12) . . ? C8 C9 C12 107.3(10) . . ? C10 C9 C12 109.0(11) . . ? C8 C9 H9 111.6 . . ? C10 C9 H9 111.6 . . ? C12 C9 H9 111.5 . . ? C11 C10 C9 111.2(15) . . ? C11 C10 H10A 109.5 . . ? C9 C10 H10A 109.4 . . ? C11 C10 H10B 109.3 . . ? C9 C10 H10B 109.4 . . ? H10A C10 H10B 108.0 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.6 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.4 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C13 C12 C9 109.6(15) . . ? C13 C12 H12A 109.6 . . ? C9 C12 H12A 109.7 . . ? C13 C12 H12B 109.9 . . ? C9 C12 H12B 109.8 . . ? H12A C12 H12B 108.2 . . ? C12 C13 H13A 109.4 . . ? C12 C13 H13B 109.4 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.6 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C15 C14 C19 117.2(9) . . ? C15 C14 C20 122.2(8) . . ? C19 C14 C20 120.5(8) . . ? C16 C15 C14 121.4(9) . . ? C16 C15 H15 119.3 . . ? C14 C15 H15 119.3 . . ? C17 C16 C15 121.2(9) . . ? C17 C16 H16 119.4 . . ? C15 C16 H16 119.4 . . ? C16 C17 C18 118.1(10) . . ? C16 C17 H17 120.9 . . ? C18 C17 H17 121.0 . . ? C19 C18 C17 121.0(10) . . ? C19 C18 H18 119.5 . . ? C17 C18 H18 119.5 . . ? C18 C19 C14 120.7(9) . . ? C18 C19 H19 119.6 . . ? C14 C19 H19 119.6 . . ? N1 C20 C14 110.8(8) . . ? N1 C20 C21 110.4(8) . . ? C14 C20 C21 113.2(8) . . ? N1 C20 H20 107.4 . . ? C14 C20 H20 107.3 . . ? C21 C20 H20 107.4 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C20 N1 H1A 109.5 . . ? C20 N1 H1B 109.5 . . ? H1A N1 H1B 109.5 . . ? C20 N1 H1C 109.5 . . ? H1A N1 H1C 109.5 . . ? H1B N1 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 C6 C1 C2 C3 0.3(15) . . . . ? C8 C1 C2 C3 179.6(10) . . . . ? C1 C2 C3 C4 2.3(16) . . . . ? C2 C3 C4 C7 178.4(9) . . . . ? C2 C3 C4 C5 -0.7(14) . . . . ? C3 C4 C5 C6 -3.4(12) . . . . ? C7 C4 C5 C6 177.5(8) . . . . ? C2 C1 C6 C5 -5.0(15) . . . . ? C8 C1 C6 C5 175.7(10) . . . . ? C4 C5 C6 C1 6.6(14) . . . . ? C3 C4 C7 O2 -141.8(10) . . . . ? C5 C4 C7 O2 37.2(12) . . . . ? C3 C4 C7 O1 35.6(12) . . . . ? C5 C4 C7 O1 -145.4(9) . . . . ? C6 C1 C8 O3 9.6(17) . . . . ? C2 C1 C8 O3 -169.7(12) . . . . ? C6 C1 C8 C9 -170.6(10) . . . . ? C2 C1 C8 C9 10.1(16) . . . . ? O3 C8 C9 C10 59.2(15) . . . . ? C1 C8 C9 C10 -120.6(13) . . . . ? O3 C8 C9 C12 -56.9(16) . . . . ? C1 C8 C9 C12 123.2(12) . . . . ? C8 C9 C10 C11 66(2) . . . . ? C12 C9 C10 C11 -178.9(19) . . . . ? C8 C9 C12 C13 -58.0(19) . . . . ? C10 C9 C12 C13 -171.8(18) . . . . ? C19 C14 C15 C16 -3.1(15) . . . . ? C20 C14 C15 C16 -179.5(9) . . . . ? C14 C15 C16 C17 3.4(16) . . . . ? C15 C16 C17 C18 -4.5(16) . . . . ? C16 C17 C18 C19 5.6(15) . . . . ? C17 C18 C19 C14 -5.6(15) . . . . ? C15 C14 C19 C18 4.2(14) . . . . ? C20 C14 C19 C18 -179.4(8) . . . . ? C15 C14 C20 N1 -124.7(9) . . . . ? C19 C14 C20 N1 59.0(11) . . . . ? C15 C14 C20 C21 110.6(10) . . . . ? C19 C14 C20 C21 -65.7(11) . . . . ? _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 22.54 _diffrn_measured_fraction_theta_full 0.973 _refine_diff_density_max 0.858 _refine_diff_density_min -0.678 _refine_diff_density_rms 0.265 #===END data_js197 _database_code_depnum_ccdc_archive 'CCDC 297458' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H19 N O' _chemical_formula_weight 229.31 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' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 9.4944(2) _cell_length_b 10.6542(3) _cell_length_c 12.8614(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1301.00(5) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.171 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 0.073 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19079 _diffrn_reflns_av_R_equivalents 0.0397 _diffrn_reflns_av_sigmaI/netI 0.0414 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.48 _diffrn_reflns_theta_max 27.89 _reflns_number_total 3106 _reflns_number_gt 2470 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0616P)^2^+0.3034P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 2(2) _refine_ls_number_reflns 3106 _refine_ls_number_parameters 69 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0681 _refine_ls_R_factor_gt 0.0514 _refine_ls_wR_factor_ref 0.1303 _refine_ls_wR_factor_gt 0.1243 _refine_ls_goodness_of_fit_ref 1.126 _refine_ls_restrained_S_all 1.126 _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 O1 O 1.04371(15) 0.19462(13) 0.16203(11) 0.0305(4) Uiso 1 1 d . . . C3 C 0.85742(19) 0.33996(16) 0.12148(15) 0.0196(4) Uiso 1 1 d . . . N1 N 0.53530(19) -0.33674(18) 0.12276(15) 0.0359(4) Uiso 1 1 d . . . C6 C 0.7425(2) 0.37403(19) 0.20198(15) 0.0247(4) Uiso 1 1 d . . . H6A H 0.7025 0.4546 0.1829 0.030 Uiso 1 1 calc R . . H6B H 0.6679 0.3121 0.1974 0.030 Uiso 1 1 calc R . . C9 C 0.82794(19) 0.09359(16) 0.14178(15) 0.0209(4) Uiso 1 1 d . . . C2 C 0.9784(2) 0.43583(19) 0.12250(17) 0.0262(4) Uiso 1 1 d . . . H2A H 1.0217 0.4350 0.1908 0.031 Uiso 1 1 calc R . . H2B H 1.0491 0.4093 0.0727 0.031 Uiso 1 1 calc R . . C8 C 0.91884(18) 0.21039(16) 0.14537(14) 0.0204(4) Uiso 1 1 d . . . C12 C 0.6774(2) -0.12982(17) 0.13369(15) 0.0245(4) Uiso 1 1 d . . . C15 C 0.5990(2) -0.24533(18) 0.12812(16) 0.0268(4) Uiso 1 1 d . . . C10 C 0.8585(2) 0.00405(18) 0.06614(17) 0.0263(4) Uiso 1 1 d . . . H10 H 0.9301 0.0192 0.0184 0.032 Uiso 1 1 calc R . . C14 C 0.7216(2) 0.06905(19) 0.21367(15) 0.0247(4) Uiso 1 1 d . . . H14 H 0.7006 0.1282 0.2645 0.030 Uiso 1 1 calc R . . C13 C 0.6473(2) -0.04217(18) 0.21025(16) 0.0268(4) Uiso 1 1 d . . . H13 H 0.5773 -0.0583 0.2591 0.032 Uiso 1 1 calc R . . C1 C 0.9351(2) 0.5702(2) 0.09694(17) 0.0336(5) Uiso 1 1 d . . . H1A H 1.0165 0.6236 0.0989 0.050 Uiso 1 1 calc R . . H1B H 0.8674 0.5988 0.1471 0.050 Uiso 1 1 calc R . . H1C H 0.8941 0.5728 0.0287 0.050 Uiso 1 1 calc R . . C5 C 0.8798(2) 0.3069(2) -0.07833(17) 0.0332(5) Uiso 1 1 d . . . H5A H 0.8242 0.3034 -0.1406 0.050 Uiso 1 1 calc R . . H5B H 0.9276 0.2284 -0.0687 0.050 Uiso 1 1 calc R . . H5C H 0.9478 0.3732 -0.0841 0.050 Uiso 1 1 calc R . . C4 C 0.7844(2) 0.33182(18) 0.01427(15) 0.0234(4) Uiso 1 1 d . . . H4A H 0.7143 0.2656 0.0173 0.028 Uiso 1 1 calc R . . H4B H 0.7348 0.4101 0.0021 0.028 Uiso 1 1 calc R . . C7 C 0.7915(2) 0.3813(2) 0.31460(17) 0.0338(5) Uiso 1 1 d . . . H7A H 0.7132 0.4029 0.3583 0.051 Uiso 1 1 calc R . . H7B H 0.8634 0.4441 0.3209 0.051 Uiso 1 1 calc R . . H7C H 0.8286 0.3014 0.3355 0.051 Uiso 1 1 calc R . . C11 C 0.7837(2) -0.10727(19) 0.06128(17) 0.0283(5) Uiso 1 1 d . . . H11 H 0.8040 -0.1664 0.0102 0.034 Uiso 1 1 calc R . . _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 C8 1.216(2) . ? C3 C8 1.530(2) . ? C3 C2 1.537(3) . ? C3 C4 1.546(3) . ? C3 C6 1.547(3) . ? N1 C15 1.149(3) . ? C6 C7 1.523(3) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C9 C10 1.393(3) . ? C9 C14 1.393(3) . ? C9 C8 1.515(2) . ? C2 C1 1.526(3) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C12 C13 1.387(3) . ? C12 C11 1.394(3) . ? C12 C15 1.440(3) . ? C10 C11 1.384(3) . ? C10 H10 0.9300 . ? C14 C13 1.380(3) . ? C14 H14 0.9300 . ? C13 H13 0.9300 . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C5 C4 1.520(3) . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C11 H11 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 C8 C3 C2 108.25(14) . . ? C8 C3 C4 107.43(15) . . ? C2 C3 C4 112.35(15) . . ? C8 C3 C6 110.25(15) . . ? C2 C3 C6 111.42(15) . . ? C4 C3 C6 107.08(15) . . ? C7 C6 C3 115.67(17) . . ? C7 C6 H6A 108.4 . . ? C3 C6 H6A 108.4 . . ? C7 C6 H6B 108.4 . . ? C3 C6 H6B 108.4 . . ? H6A C6 H6B 107.4 . . ? C10 C9 C14 119.07(17) . . ? C10 C9 C8 117.71(16) . . ? C14 C9 C8 123.13(16) . . ? C1 C2 C3 114.86(16) . . ? C1 C2 H2A 108.6 . . ? C3 C2 H2A 108.6 . . ? C1 C2 H2B 108.6 . . ? C3 C2 H2B 108.6 . . ? H2A C2 H2B 107.5 . . ? O1 C8 C9 116.56(16) . . ? O1 C8 C3 122.11(16) . . ? C9 C8 C3 121.19(14) . . ? C13 C12 C11 120.50(18) . . ? C13 C12 C15 120.29(18) . . ? C11 C12 C15 119.21(18) . . ? N1 C15 C12 179.1(2) . . ? C11 C10 C9 120.7(2) . . ? C11 C10 H10 119.6 . . ? C9 C10 H10 119.6 . . ? C13 C14 C9 120.70(18) . . ? C13 C14 H14 119.7 . . ? C9 C14 H14 119.7 . . ? C14 C13 C12 119.69(19) . . ? C14 C13 H13 120.2 . . ? C12 C13 H13 120.2 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C5 C4 C3 116.19(16) . . ? C5 C4 H4A 108.2 . . ? C3 C4 H4A 108.2 . . ? C5 C4 H4B 108.2 . . ? C3 C4 H4B 108.2 . . ? H4A C4 H4B 107.4 . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C10 C11 C12 119.29(19) . . ? C10 C11 H11 120.4 . . ? C12 C11 H11 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 C8 C3 C6 C7 60.9(2) . . . . ? C2 C3 C6 C7 -59.3(2) . . . . ? C4 C3 C6 C7 177.45(16) . . . . ? C8 C3 C2 C1 178.40(17) . . . . ? C4 C3 C2 C1 59.9(2) . . . . ? C6 C3 C2 C1 -60.2(2) . . . . ? C10 C9 C8 O1 -61.1(2) . . . . ? C14 C9 C8 O1 115.2(2) . . . . ? C10 C9 C8 C3 114.7(2) . . . . ? C14 C9 C8 C3 -69.0(2) . . . . ? C2 C3 C8 O1 0.4(2) . . . . ? C4 C3 C8 O1 121.94(19) . . . . ? C6 C3 C8 O1 -121.71(19) . . . . ? C2 C3 C8 C9 -175.17(16) . . . . ? C4 C3 C8 C9 -53.6(2) . . . . ? C6 C3 C8 C9 62.7(2) . . . . ? C13 C12 C15 N1 92(16) . . . . ? C11 C12 C15 N1 -88(16) . . . . ? C14 C9 C10 C11 0.8(3) . . . . ? C8 C9 C10 C11 177.21(18) . . . . ? C10 C9 C14 C13 -0.1(3) . . . . ? C8 C9 C14 C13 -176.32(18) . . . . ? C9 C14 C13 C12 -0.8(3) . . . . ? C11 C12 C13 C14 1.0(3) . . . . ? C15 C12 C13 C14 -178.95(19) . . . . ? C8 C3 C4 C5 -65.2(2) . . . . ? C2 C3 C4 C5 53.8(2) . . . . ? C6 C3 C4 C5 176.41(17) . . . . ? C9 C10 C11 C12 -0.5(3) . . . . ? C13 C12 C11 C10 -0.4(3) . . . . ? C15 C12 C11 C10 179.62(19) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.89 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.423 _refine_diff_density_min -0.363 _refine_diff_density_rms 0.051