#------------------------------------------------------------------------------ #$Date: 2013-12-28 07:07:06 +0000 (Sat, 28 Dec 2013) $ #$Revision: 91932 $ #$URL: svn://www.crystallography.net/cod/cif/1/50/78/1507869.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_1507869 loop_ _publ_author_name 'Snyder, Seth E.' 'Huang, Bin-Syuan' 'Chen, Yu-Tzu' 'Lin, Huei-Shian' 'Carey, James R.' _publ_section_title ; A Simple Chiral Recognition System to Investigate Substituent Effects on \p--\p Interactions ; _journal_issue 13 _journal_name_full 'Organic Letters' _journal_page_first 3442 _journal_volume 14 _journal_year 2012 _chemical_formula_moiety 'C18 H28 N2 O2' _chemical_formula_sum 'C18 H28 N2 O2' _chemical_formula_weight 304.42 _space_group_IT_number 15 _symmetry_cell_setting monoclinic _symmetry_Int_Tables_number 15 _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 117.843(6) _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 19.5529(9) _cell_length_b 10.7474(4) _cell_length_c 19.5495(10) _cell_measurement_reflns_used 3680 _cell_measurement_temperature 110(2) _cell_measurement_theta_max 28.9958 _cell_measurement_theta_min 3.0804 _cell_volume 3632.6(3) _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) (compiled Jun 10 2008,16:49:55) ; _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _diffrn_ambient_temperature 110(2) _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.860 _diffrn_measurement_device_type 'CCD detector' _diffrn_measurement_method 'omega scan' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0161 _diffrn_reflns_av_sigmaI/netI 0.0367 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_number 8203 _diffrn_reflns_theta_full 26.00 _diffrn_reflns_theta_max 29.05 _diffrn_reflns_theta_min 3.62 _diffrn_source 'fine-focus sealed tube' _exptl_absorpt_coefficient_mu 0.072 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.98725 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.46 (release 27-08-2009 CrysAlis171 .NET) (compiled Aug 27 2009,17:19:36) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.113 _exptl_crystal_density_method 'not measured' _exptl_crystal_description parallelepiped _exptl_crystal_F_000 1328 _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.42 _refine_diff_density_max 0.349 _refine_diff_density_min -0.310 _refine_diff_density_rms 0.039 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 219 _refine_ls_number_reflns 4184 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.030 _refine_ls_R_factor_all 0.0848 _refine_ls_R_factor_gt 0.0549 _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^)+(0.0998P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1556 _refine_ls_wR_factor_ref 0.1670 _reflns_number_gt 2696 _reflns_number_total 4184 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file ol3014057_si_002.cif _[local]_cod_data_source_block 1b _[local]_cod_cif_authors_sg_H-M 'C 2/c' _cod_database_code 1507869 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' 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 0.17046(7) 0.39258(12) 0.32430(8) 0.0493(4) Uani 1 1 d . . . O2 O 0.03080(6) 0.09430(11) 0.17642(7) 0.0385(3) Uani 1 1 d . . . N1 N 0.09509(8) 0.22818(13) 0.31414(8) 0.0306(3) Uani 1 1 d . . . H1A H 0.0546(11) 0.2004(17) 0.3148(10) 0.039(5) Uiso 1 1 d . . . N2 N 0.14640(7) 0.08595(13) 0.17709(8) 0.0350(3) Uani 1 1 d . . . C1 C 0.01320(9) 0.38246(18) 0.37352(10) 0.0406(4) Uani 1 1 d . A . H1B H 0.0099 0.2950 0.3783 0.049 Uiso 1 1 calc R . . C2 C -0.03241(11) 0.4605(2) 0.39212(13) 0.0543(5) Uani 1 1 d . . . C3 C -0.02708(15) 0.5864(2) 0.38443(17) 0.0762(8) Uani 1 1 d . A . H3A H -0.0583 0.6404 0.3966 0.091 Uiso 1 1 calc R . . C4 C 0.02188(17) 0.6364(2) 0.35983(19) 0.0832(9) Uani 1 1 d . . . C5 C 0.06818(14) 0.5563(2) 0.34220(15) 0.0642(6) Uani 1 1 d . A . H5A H 0.1032 0.5900 0.3260 0.077 Uiso 1 1 calc R . . C6 C 0.06321(10) 0.42929(17) 0.34825(10) 0.0399(4) Uani 1 1 d . . . C7 C 0.11383(9) 0.34879(16) 0.32764(10) 0.0347(4) Uani 1 1 d . A . C8 C 0.14194(9) 0.14174(15) 0.29680(9) 0.0300(4) Uani 1 1 d . . . H8A H 0.1922 0.1829 0.3090 0.036 Uiso 1 1 calc R . . C9 C 0.10177(9) 0.10615(15) 0.21159(9) 0.0308(4) Uani 1 1 d . . . C10 C 0.10969(11) 0.0520(2) 0.09491(11) 0.0471(5) Uani 1 1 d . . . H10A H 0.1361 0.0966 0.0696 0.057 Uiso 1 1 calc R . . H10B H 0.0551 0.0799 0.0702 0.057 Uiso 1 1 calc R . . C11 C 0.11186(14) -0.0849(2) 0.08158(15) 0.0697(7) Uani 1 1 d . . . H11A H 0.0866 -0.1016 0.0259 0.105 Uiso 1 1 calc R . . H11B H 0.0846 -0.1296 0.1053 0.105 Uiso 1 1 calc R . . H11C H 0.1657 -0.1129 0.1048 0.105 Uiso 1 1 calc R . . C12 C 0.23108(9) 0.09720(18) 0.21610(11) 0.0413(4) Uani 1 1 d . . . H12A H 0.2526 0.0363 0.1933 0.050 Uiso 1 1 calc R . . H12B H 0.2512 0.0760 0.2715 0.050 Uiso 1 1 calc R . . C13 C 0.25876(12) 0.2262(2) 0.20980(12) 0.0568(6) Uani 1 1 d . . . H13A H 0.3154 0.2285 0.2374 0.085 Uiso 1 1 calc R . . H13B H 0.2381 0.2870 0.2327 0.085 Uiso 1 1 calc R . . H13C H 0.2407 0.2466 0.1552 0.085 Uiso 1 1 calc R . . C14 C 0.15866(10) 0.02371(16) 0.34654(10) 0.0368(4) Uani 1 1 d . . . H14A H 0.1089 -0.0157 0.3357 0.044 Uiso 1 1 calc R . . H14B H 0.1875 -0.0357 0.3309 0.044 Uiso 1 1 calc R . . C15 C 0.20478(11) 0.04653(19) 0.43312(10) 0.0474(5) Uani 1 1 d . . . H15A H 0.1720 0.0980 0.4490 0.057 Uiso 1 1 calc R . . C16 C 0.27902(14) 0.1177(3) 0.45490(15) 0.0960(11) Uani 1 1 d . . . H16A H 0.2670 0.1966 0.4265 0.144 Uiso 1 1 calc R . . H16B H 0.3132 0.0681 0.4416 0.144 Uiso 1 1 calc R . . H16C H 0.3048 0.1345 0.5106 0.144 Uiso 1 1 calc R . . C17 C 0.22108(14) -0.0762(2) 0.47676(12) 0.0623(6) Uani 1 1 d . . . H17A H 0.1723 -0.1200 0.4622 0.093 Uiso 1 1 calc R . . H17B H 0.2469 -0.0599 0.5325 0.093 Uiso 1 1 calc R . . H17C H 0.2546 -0.1277 0.4636 0.093 Uiso 1 1 calc R . . C18 C -0.0858(2) 0.4146(5) 0.4154(3) 0.0762(19) Uani 0.533(6) 1 d P A 1 H18A H -0.1385 0.4273 0.3737 0.099(17) Uiso 0.533(6) 1 calc PR A 1 H18B H -0.0793 0.4590 0.4618 0.18(3) Uiso 0.533(6) 1 calc PR A 1 H18C H -0.0768 0.3255 0.4268 0.15(3) Uiso 0.533(6) 1 calc PR A 1 C18' C 0.0123(3) 0.7666(4) 0.3337(4) 0.080(2) Uani 0.467(6) 1 d P A 2 H18D H 0.0436 0.7821 0.3074 0.12(2) Uiso 0.467(6) 1 calc PR A 2 H18E H 0.0292 0.8221 0.3785 0.12(2) Uiso 0.467(6) 1 calc PR A 2 H18F H -0.0423 0.7825 0.2978 0.15(3) Uiso 0.467(6) 1 calc PR A 2 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 0.0479(7) 0.0367(7) 0.0712(10) 0.0036(7) 0.0344(7) -0.0027(6) O2 0.0336(6) 0.0430(7) 0.0449(7) -0.0066(6) 0.0234(5) -0.0014(5) N1 0.0285(7) 0.0310(7) 0.0386(8) 0.0000(6) 0.0210(6) 0.0024(6) N2 0.0374(7) 0.0396(8) 0.0369(8) 0.0027(6) 0.0249(6) 0.0035(6) C1 0.0359(8) 0.0425(10) 0.0421(10) -0.0094(8) 0.0170(7) 0.0058(8) C2 0.0488(11) 0.0512(13) 0.0645(13) -0.0169(11) 0.0278(10) 0.0065(10) C3 0.0783(16) 0.0512(14) 0.117(2) -0.0085(14) 0.0608(16) 0.0168(13) C4 0.103(2) 0.0342(12) 0.135(3) -0.0003(14) 0.075(2) 0.0150(13) C5 0.0745(14) 0.0396(12) 0.0917(18) 0.0092(12) 0.0498(13) 0.0130(11) C6 0.0408(9) 0.0350(10) 0.0369(9) -0.0008(8) 0.0124(7) 0.0100(8) C7 0.0327(8) 0.0351(9) 0.0356(9) 0.0041(7) 0.0154(7) 0.0031(7) C8 0.0305(7) 0.0296(8) 0.0379(9) 0.0036(7) 0.0227(7) 0.0044(7) C9 0.0352(8) 0.0251(8) 0.0405(9) 0.0040(7) 0.0248(7) 0.0030(7) C10 0.0488(10) 0.0609(13) 0.0415(11) -0.0039(9) 0.0294(8) -0.0021(9) C11 0.0713(14) 0.0672(16) 0.0729(16) -0.0249(13) 0.0355(12) -0.0133(13) C12 0.0389(9) 0.0498(11) 0.0472(10) 0.0011(9) 0.0300(8) 0.0042(8) C13 0.0536(11) 0.0675(15) 0.0594(13) -0.0019(11) 0.0347(10) -0.0159(11) C14 0.0470(9) 0.0329(9) 0.0443(10) 0.0081(8) 0.0329(8) 0.0093(8) C15 0.0572(11) 0.0486(12) 0.0430(11) 0.0126(9) 0.0288(9) 0.0148(10) C16 0.0657(15) 0.125(3) 0.0574(16) 0.0371(16) -0.0045(11) -0.0164(16) C17 0.0907(16) 0.0620(14) 0.0490(12) 0.0232(11) 0.0450(12) 0.0276(13) C18 0.046(2) 0.089(4) 0.098(4) -0.049(3) 0.036(2) 0.002(2) C18' 0.088(4) 0.032(3) 0.157(6) -0.027(3) 0.087(4) -0.017(3) 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C7 N1 C8 121.40(13) C7 N1 H1A 120.4(12) C8 N1 H1A 118.2(13) C9 N2 C10 119.24(13) C9 N2 C12 124.30(14) C10 N2 C12 116.45(12) C6 C1 C2 121.45(18) C6 C1 H1B 119.3 C2 C1 H1B 119.3 C3 C2 C1 118.4(2) C3 C2 C18 119.1(3) C1 C2 C18 122.4(3) C4 C3 C2 121.9(2) C4 C3 H3A 119.1 C2 C3 H3A 119.1 C3 C4 C5 118.9(2) C3 C4 C18' 120.0(3) C5 C4 C18' 119.3(3) C6 C5 C4 120.5(2) C6 C5 H5A 119.8 C4 C5 H5A 119.8 C5 C6 C1 118.83(17) C5 C6 C7 117.74(17) C1 C6 C7 123.43(16) O1 C7 N1 121.93(15) O1 C7 C6 120.95(16) N1 C7 C6 117.11(14) N1 C8 C9 110.93(12) N1 C8 C14 110.56(12) C9 C8 C14 109.48(14) N1 C8 H8A 108.6 C9 C8 H8A 108.6 C14 C8 H8A 108.6 O2 C9 N2 121.83(15) O2 C9 C8 120.46(12) N2 C9 C8 117.70(13) N2 C10 C11 113.29(18) N2 C10 H10A 108.9 C11 C10 H10A 108.9 N2 C10 H10B 108.9 C11 C10 H10B 108.9 H10A C10 H10B 107.7 C10 C11 H11A 109.5 C10 C11 H11B 109.5 H11A C11 H11B 109.5 C10 C11 H11C 109.5 H11A C11 H11C 109.5 H11B C11 H11C 109.5 N2 C12 C13 113.08(15) N2 C12 H12A 109.0 C13 C12 H12A 109.0 N2 C12 H12B 109.0 C13 C12 H12B 109.0 H12A C12 H12B 107.8 C12 C13 H13A 109.5 C12 C13 H13B 109.5 H13A C13 H13B 109.5 C12 C13 H13C 109.5 H13A C13 H13C 109.5 H13B C13 H13C 109.5 C15 C14 C8 114.29(15) C15 C14 H14A 108.7 C8 C14 H14A 108.7 C15 C14 H14B 108.7 C8 C14 H14B 108.7 H14A C14 H14B 107.6 C16 C15 C14 112.72(16) C16 C15 C17 110.97(18) C14 C15 C17 110.15(17) C16 C15 H15A 107.6 C14 C15 H15A 107.6 C17 C15 H15A 107.6 C15 C16 H16A 109.5 C15 C16 H16B 109.5 H16A C16 H16B 109.5 C15 C16 H16C 109.5 H16A C16 H16C 109.5 H16B C16 H16C 109.5 C15 C17 H17A 109.5 C15 C17 H17B 109.5 H17A C17 H17B 109.5 C15 C17 H17C 109.5 H17A C17 H17C 109.5 H17B C17 H17C 109.5 C2 C18 H18A 109.5 C2 C18 H18B 109.5 H18A C18 H18B 109.5 C2 C18 H18C 109.5 H18A C18 H18C 109.5 H18B C18 H18C 109.5 C4 C18' H18D 109.5 C4 C18' H18E 109.5 H18D C18' H18E 109.5 C4 C18' H18F 109.5 H18D C18' H18F 109.5 H18E C18' H18F 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C7 1.2326(19) O2 C9 1.2343(19) N1 C7 1.339(2) N1 C8 1.4516(19) N1 H1A 0.851(18) N2 C9 1.3466(19) N2 C10 1.467(2) N2 C12 1.469(2) C1 C6 1.380(2) C1 C2 1.390(2) C1 H1B 0.9500 C2 C3 1.371(3) C2 C18 1.408(5) C3 C4 1.366(3) C3 H3A 0.9500 C4 C5 1.403(3) C4 C18' 1.472(5) C5 C6 1.378(3) C5 H5A 0.9500 C6 C7 1.504(2) C8 C9 1.522(2) C8 C14 1.538(2) C8 H8A 1.0000 C10 C11 1.498(3) C10 H10A 0.9900 C10 H10B 0.9900 C11 H11A 0.9800 C11 H11B 0.9800 C11 H11C 0.9800 C12 C13 1.514(3) C12 H12A 0.9900 C12 H12B 0.9900 C13 H13A 0.9800 C13 H13B 0.9800 C13 H13C 0.9800 C14 C15 1.521(2) C14 H14A 0.9900 C14 H14B 0.9900 C15 C16 1.515(3) C15 C17 1.521(3) C15 H15A 1.0000 C16 H16A 0.9800 C16 H16B 0.9800 C16 H16C 0.9800 C17 H17A 0.9800 C17 H17B 0.9800 C17 H17C 0.9800 C18 H18A 0.9800 C18 H18B 0.9800 C18 H18C 0.9800 C18' H18D 0.9800 C18' H18E 0.9800 C18' H18F 0.9800 _journal_paper_doi 10.1021/ol3014057