# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_4ab _audit_creation_date 2013-08-23 _audit_creation_method ; Olex2 1.1 (compiled 2011.11.01 svn.r2039, GUI svn.r3906) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety '0.03(C92 H76 N4)' _chemical_formula_sum 'C8.25 H8.25 N8.25 O8.25' _chemical_formula_weight 354.98 _chemical_absolute_configuration unk _chemical_melting_point ? _chemical_oxdiff_formula C1H1N1O1 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 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 7.5579(6) _cell_length_b 12.3380(10) _cell_length_c 18.5927(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1733.7(2) _cell_formula_units_Z 33 _cell_measurement_reflns_used 1072 _cell_measurement_temperature 291(2) _cell_measurement_theta_max 23.7510 _cell_measurement_theta_min 3.4640 _exptl_absorpt_coefficient_mu 0.122 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.96021 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_density_diffrn 1.360 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 726 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0317 _diffrn_reflns_av_unetI/netI 0.0585 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 4636 _diffrn_reflns_theta_full 26.37 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_min 3.16 _diffrn_ambient_temperature 291.15 _diffrn_detector_area_resol_mean 16.2312 _diffrn_measured_fraction_theta_full 0.9947 _diffrn_measured_fraction_theta_max 0.7128 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -10.00 17.00 1.0000 6.9700 omega____ theta____ kappa____ phi______ frames - -17.2885 -99.0000 -150.0000 27 #__ type_ start__ end____ width___ exp.time_ 2 omega -33.00 1.00 1.0000 6.9700 omega____ theta____ kappa____ phi______ frames - 19.7885 -19.0000 -120.0000 34 #__ type_ start__ end____ width___ exp.time_ 3 omega 4.00 64.00 1.0000 6.9700 omega____ theta____ kappa____ phi______ frames - 19.7885 -19.0000 -120.0000 60 #__ type_ start__ end____ width___ exp.time_ 4 omega -7.00 19.00 1.0000 6.9700 omega____ theta____ kappa____ phi______ frames - 19.7885 -57.0000 -30.0000 26 ; _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0904229000 _diffrn_orient_matrix_UB_12 -0.0153540000 _diffrn_orient_matrix_UB_13 -0.0020149000 _diffrn_orient_matrix_UB_21 0.0199591000 _diffrn_orient_matrix_UB_22 0.0490867000 _diffrn_orient_matrix_UB_23 -0.0181071000 _diffrn_orient_matrix_UB_31 0.0160179000 _diffrn_orient_matrix_UB_32 0.0255254000 _diffrn_orient_matrix_UB_33 0.0335140000 _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 n/a _diffrn_source_voltage n/a _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 2195 _reflns_number_total 3014 _reflns_odcompleteness_completeness 99.47 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _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 ; XL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; XS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.130 _refine_diff_density_min -0.183 _refine_diff_density_rms 0.035 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -8(6) _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 218 _refine_ls_number_reflns 3014 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0839 _refine_ls_R_factor_gt 0.0599 _refine_ls_restrained_S_all 1.047 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0646P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1336 _refine_ls_wR_factor_ref 0.1548 _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 N1 N 0.7723(3) 0.29694(19) 0.14995(12) 0.0457(6) Uani 1 1 d . . . H1 H 0.7084 0.3364 0.1220 0.055 Uiso 1 1 calc R . . C1 C 0.8581(4) 0.2034(2) 0.12956(13) 0.0420(6) Uani 1 1 d . . . C2 C 0.9486(4) 0.1670(3) 0.18853(13) 0.0464(7) Uani 1 1 d . . . H2 H 1.0203 0.1058 0.1900 0.056 Uiso 1 1 calc R . . C3 C 0.9150(4) 0.2379(2) 0.24689(14) 0.0451(7) Uani 1 1 d . . . C4 C 0.8040(4) 0.3184(2) 0.22201(14) 0.0441(7) Uani 1 1 d . . . C5 C 0.7267(4) 0.4140(2) 0.25715(16) 0.0474(7) Uani 1 1 d . . . C6 C 0.6724(4) 0.5039(3) 0.21793(18) 0.0588(8) Uani 1 1 d . . . H6 H 0.6902 0.5055 0.1684 0.071 Uiso 1 1 calc R . . C7 C 0.5921(4) 0.5912(3) 0.2515(2) 0.0758(11) Uani 1 1 d . . . H7 H 0.5549 0.6502 0.2242 0.091 Uiso 1 1 calc R . . C8 C 0.5670(5) 0.5917(3) 0.3244(2) 0.0791(12) Uani 1 1 d . . . H8 H 0.5120 0.6502 0.3466 0.095 Uiso 1 1 calc R . . C9 C 0.6240(5) 0.5047(3) 0.3643(2) 0.0761(11) Uani 1 1 d . . . H9 H 0.6106 0.5056 0.4141 0.091 Uiso 1 1 calc R . . C10 C 0.7009(4) 0.4158(3) 0.33158(16) 0.0615(9) Uani 1 1 d . . . H10 H 0.7358 0.3567 0.3593 0.074 Uiso 1 1 calc R . . C11 C 0.8507(4) 0.1618(2) 0.05612(14) 0.0450(7) Uani 1 1 d . . . C12 C 0.7704(5) 0.2171(3) -0.00007(16) 0.0601(9) Uani 1 1 d . . . H12 H 0.7149 0.2829 0.0091 0.072 Uiso 1 1 calc R . . C13 C 0.7710(5) 0.1766(3) -0.06886(16) 0.0651(10) Uani 1 1 d . . . H13 H 0.7137 0.2143 -0.1054 0.078 Uiso 1 1 calc R . . C14 C 0.8557(5) 0.0808(3) -0.08408(15) 0.0594(9) Uani 1 1 d . . . H14 H 0.8599 0.0548 -0.1310 0.071 Uiso 1 1 calc R . . C15 C 0.9338(5) 0.0243(3) -0.02955(16) 0.0670(10) Uani 1 1 d . . . H15 H 0.9898 -0.0412 -0.0393 0.080 Uiso 1 1 calc R . . C16 C 0.9305(5) 0.0632(3) 0.03964(15) 0.0578(9) Uani 1 1 d . . . H16 H 0.9826 0.0229 0.0762 0.069 Uiso 1 1 calc R . . C17 C 0.9974(4) 0.2276(3) 0.31921(14) 0.0504(8) Uani 1 1 d . . . C18 C 0.9392(5) 0.1466(3) 0.36546(16) 0.0688(10) Uani 1 1 d . . . H18 H 0.8465 0.1018 0.3513 0.083 Uiso 1 1 calc R . . C19 C 1.0159(6) 0.1313(4) 0.43144(18) 0.0874(13) Uani 1 1 d . . . H19 H 0.9756 0.0767 0.4618 0.105 Uiso 1 1 calc R . . C20 C 1.1528(7) 0.1974(4) 0.45238(17) 0.0885(14) Uani 1 1 d . . . H20 H 1.2050 0.1879 0.4972 0.106 Uiso 1 1 calc R . . C21 C 1.2126(5) 0.2774(3) 0.40722(18) 0.0764(11) Uani 1 1 d . . . H21 H 1.3047 0.3220 0.4221 0.092 Uiso 1 1 calc R . . C22 C 1.1380(4) 0.2930(3) 0.33952(15) 0.0562(8) Uani 1 1 d . . . C23 C 1.2094(5) 0.3778(3) 0.29036(19) 0.0763(10) Uani 1 1 d . . . H23A H 1.2807 0.3442 0.2539 0.114 Uiso 1 1 calc R . . H23B H 1.2803 0.4279 0.3174 0.114 Uiso 1 1 calc R . . H23C H 1.1131 0.4159 0.2681 0.114 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 N1 0.0435(13) 0.0482(13) 0.0455(12) 0.0005(11) -0.0073(11) 0.0005(12) C1 0.0364(13) 0.0440(14) 0.0455(13) -0.0018(13) 0.0007(13) -0.0010(14) C2 0.0378(14) 0.0525(17) 0.0489(15) 0.0041(14) -0.0003(13) 0.0036(15) C3 0.0410(15) 0.0486(16) 0.0458(13) 0.0007(13) -0.0026(13) -0.0034(14) C4 0.0398(15) 0.0487(16) 0.0438(14) -0.0003(13) 0.0002(12) -0.0033(14) C5 0.0338(14) 0.0504(17) 0.0581(16) -0.0085(15) -0.0018(14) -0.0028(14) C6 0.0505(18) 0.0542(18) 0.0717(19) -0.0075(18) -0.0041(17) -0.0040(18) C7 0.058(2) 0.060(2) 0.109(3) -0.012(2) -0.011(2) 0.001(2) C8 0.049(2) 0.068(2) 0.120(3) -0.038(2) 0.008(2) 0.005(2) C9 0.051(2) 0.095(3) 0.083(2) -0.030(2) 0.0132(19) -0.007(2) C10 0.0485(18) 0.075(2) 0.0606(18) -0.0099(18) 0.0066(16) 0.0004(19) C11 0.0378(14) 0.0530(17) 0.0442(13) 0.0033(14) 0.0010(13) -0.0028(15) C12 0.061(2) 0.072(2) 0.0481(14) -0.0013(17) -0.0051(15) 0.014(2) C13 0.067(2) 0.080(2) 0.0479(16) 0.0066(17) -0.0065(16) 0.006(2) C14 0.0572(19) 0.075(2) 0.0456(15) -0.0096(16) 0.0040(16) -0.006(2) C15 0.081(3) 0.061(2) 0.0591(17) -0.0080(17) -0.002(2) 0.011(2) C16 0.065(2) 0.0560(19) 0.0522(17) -0.0010(15) -0.0069(17) 0.0126(19) C17 0.0475(17) 0.061(2) 0.0422(14) -0.0029(14) -0.0015(13) -0.0021(17) C18 0.068(2) 0.087(2) 0.0520(17) 0.0168(18) -0.0009(16) -0.006(2) C19 0.096(3) 0.107(3) 0.059(2) 0.021(2) 0.004(2) 0.001(3) C20 0.100(3) 0.119(4) 0.0467(18) 0.001(2) -0.014(2) 0.012(3) C21 0.074(2) 0.096(3) 0.0598(18) -0.014(2) -0.0185(19) 0.000(3) C22 0.0526(18) 0.065(2) 0.0512(15) -0.0105(16) -0.0065(15) 0.0082(19) C23 0.062(2) 0.075(2) 0.092(2) 0.002(2) -0.009(2) -0.014(2) _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 N1 H1 0.8600 . ? N1 C1 1.377(3) . ? N1 C4 1.386(3) . ? C1 C2 1.368(4) . ? C1 C11 1.460(3) . ? C2 H2 0.9300 . ? C2 C3 1.417(4) . ? C3 C4 1.380(4) . ? C3 C17 1.487(4) . ? C4 C5 1.470(4) . ? C5 C6 1.390(4) . ? C5 C10 1.398(4) . ? C6 H6 0.9300 . ? C6 C7 1.385(4) . ? C7 H7 0.9300 . ? C7 C8 1.368(5) . ? C8 H8 0.9300 . ? C8 C9 1.375(5) . ? C9 H9 0.9300 . ? C9 C10 1.383(5) . ? C10 H10 0.9300 . ? C11 C12 1.387(4) . ? C11 C16 1.392(4) . ? C12 H12 0.9300 . ? C12 C13 1.373(4) . ? C13 H13 0.9300 . ? C13 C14 1.373(4) . ? C14 H14 0.9300 . ? C14 C15 1.365(4) . ? C15 H15 0.9300 . ? C15 C16 1.373(4) . ? C16 H16 0.9300 . ? C17 C18 1.390(4) . ? C17 C22 1.387(4) . ? C18 H18 0.9300 . ? C18 C19 1.370(4) . ? C19 H19 0.9300 . ? C19 C20 1.373(6) . ? C20 H20 0.9300 . ? C20 C21 1.373(5) . ? C21 H21 0.9300 . ? C21 C22 1.392(4) . ? C22 C23 1.490(5) . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 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 C1 N1 H1 124.9 . . ? C1 N1 C4 110.2(2) . . ? C4 N1 H1 124.9 . . ? N1 C1 C11 122.3(2) . . ? C2 C1 N1 106.9(2) . . ? C2 C1 C11 130.8(3) . . ? C1 C2 H2 125.6 . . ? C1 C2 C3 108.7(3) . . ? C3 C2 H2 125.6 . . ? C2 C3 C17 124.4(3) . . ? C4 C3 C2 107.3(2) . . ? C4 C3 C17 128.2(3) . . ? N1 C4 C5 121.0(2) . . ? C3 C4 N1 106.9(2) . . ? C3 C4 C5 132.1(2) . . ? C6 C5 C4 121.7(2) . . ? C6 C5 C10 117.8(3) . . ? C10 C5 C4 120.5(3) . . ? C5 C6 H6 119.5 . . ? C7 C6 C5 120.9(3) . . ? C7 C6 H6 119.5 . . ? C6 C7 H7 119.7 . . ? C8 C7 C6 120.7(4) . . ? C8 C7 H7 119.7 . . ? C7 C8 H8 120.4 . . ? C7 C8 C9 119.3(3) . . ? C9 C8 H8 120.4 . . ? C8 C9 H9 119.6 . . ? C8 C9 C10 120.9(3) . . ? C10 C9 H9 119.6 . . ? C5 C10 H10 119.8 . . ? C9 C10 C5 120.5(3) . . ? C9 C10 H10 119.8 . . ? C12 C11 C1 123.3(3) . . ? C12 C11 C16 117.0(3) . . ? C16 C11 C1 119.8(2) . . ? C11 C12 H12 119.3 . . ? C13 C12 C11 121.4(3) . . ? C13 C12 H12 119.3 . . ? C12 C13 H13 119.8 . . ? C12 C13 C14 120.4(3) . . ? C14 C13 H13 119.8 . . ? C13 C14 H14 120.4 . . ? C15 C14 C13 119.2(3) . . ? C15 C14 H14 120.4 . . ? C14 C15 H15 119.7 . . ? C14 C15 C16 120.6(3) . . ? C16 C15 H15 119.7 . . ? C11 C16 H16 119.3 . . ? C15 C16 C11 121.3(3) . . ? C15 C16 H16 119.3 . . ? C18 C17 C3 119.2(3) . . ? C22 C17 C3 121.2(3) . . ? C22 C17 C18 119.5(3) . . ? C17 C18 H18 119.4 . . ? C19 C18 C17 121.2(4) . . ? C19 C18 H18 119.4 . . ? C18 C19 H19 120.3 . . ? C18 C19 C20 119.4(4) . . ? C20 C19 H19 120.3 . . ? C19 C20 H20 120.0 . . ? C21 C20 C19 120.1(3) . . ? C21 C20 H20 120.0 . . ? C20 C21 H21 119.4 . . ? C20 C21 C22 121.3(4) . . ? C22 C21 H21 119.4 . . ? C17 C22 C21 118.4(3) . . ? C17 C22 C23 121.2(3) . . ? C21 C22 C23 120.3(3) . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23B 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 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 N1 C1 C2 C3 1.3(3) . . . . ? N1 C1 C11 C12 5.7(4) . . . . ? N1 C1 C11 C16 -175.9(3) . . . . ? N1 C4 C5 C6 -22.2(4) . . . . ? N1 C4 C5 C10 155.9(3) . . . . ? C1 N1 C4 C3 1.3(3) . . . . ? C1 N1 C4 C5 -179.9(2) . . . . ? C1 C2 C3 C4 -0.6(3) . . . . ? C1 C2 C3 C17 -176.9(3) . . . . ? C1 C11 C12 C13 178.0(3) . . . . ? C1 C11 C16 C15 -176.7(3) . . . . ? C2 C1 C11 C12 -171.0(3) . . . . ? C2 C1 C11 C16 7.4(5) . . . . ? C2 C3 C4 N1 -0.4(3) . . . . ? C2 C3 C4 C5 -179.1(3) . . . . ? C2 C3 C17 C18 -74.8(4) . . . . ? C2 C3 C17 C22 101.2(4) . . . . ? C3 C4 C5 C6 156.3(3) . . . . ? C3 C4 C5 C10 -25.6(5) . . . . ? C3 C17 C18 C19 177.4(3) . . . . ? C3 C17 C22 C21 -178.2(3) . . . . ? C3 C17 C22 C23 1.4(5) . . . . ? C4 N1 C1 C2 -1.6(3) . . . . ? C4 N1 C1 C11 -179.0(3) . . . . ? C4 C3 C17 C18 109.7(4) . . . . ? C4 C3 C17 C22 -74.3(4) . . . . ? C4 C5 C6 C7 176.9(3) . . . . ? C4 C5 C10 C9 -178.3(3) . . . . ? C5 C6 C7 C8 1.1(5) . . . . ? C6 C5 C10 C9 -0.1(5) . . . . ? C6 C7 C8 C9 0.6(5) . . . . ? C7 C8 C9 C10 -2.0(6) . . . . ? C8 C9 C10 C5 1.8(5) . . . . ? C10 C5 C6 C7 -1.3(4) . . . . ? C11 C1 C2 C3 178.4(3) . . . . ? C11 C12 C13 C14 -1.6(5) . . . . ? C12 C11 C16 C15 1.9(5) . . . . ? C12 C13 C14 C15 2.4(5) . . . . ? C13 C14 C15 C16 -1.0(5) . . . . ? C14 C15 C16 C11 -1.1(5) . . . . ? C16 C11 C12 C13 -0.5(5) . . . . ? C17 C3 C4 N1 175.7(3) . . . . ? C17 C3 C4 C5 -2.9(5) . . . . ? C17 C18 C19 C20 0.0(6) . . . . ? C18 C17 C22 C21 -2.2(5) . . . . ? C18 C17 C22 C23 177.4(3) . . . . ? C18 C19 C20 C21 -0.4(6) . . . . ? C19 C20 C21 C22 -0.6(6) . . . . ? C20 C21 C22 C17 1.9(5) . . . . ? C20 C21 C22 C23 -177.8(3) . . . . ? C22 C17 C18 C19 1.3(5) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 957206' ####################################################################### # # 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_4ca _audit_creation_date 2013-08-23 _audit_creation_method ; Olex2 1.1 (compiled 2011.11.01 svn.r2039, GUI svn.r3906) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C23 H19 N' _chemical_formula_sum 'C23 H19 N' _chemical_formula_weight 309.39 _chemical_absolute_configuration unk _chemical_melting_point ? _chemical_oxdiff_formula C1H1N1O1 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' _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 7.5359(11) _cell_length_b 12.7094(13) _cell_length_c 18.190(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1742.2(4) _cell_formula_units_Z 4 _cell_measurement_reflns_used 956 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 23.6630 _cell_measurement_theta_min 3.3740 _exptl_absorpt_coefficient_mu 0.068 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.94990 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_density_diffrn 1.180 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0334 _diffrn_reflns_av_unetI/netI 0.0709 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 4795 _diffrn_reflns_theta_full 26.37 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_min 3.14 _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 16.2312 _diffrn_measured_fraction_theta_full 0.9966 _diffrn_measured_fraction_theta_max 0.7545 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -16.00 26.00 1.0000 1.8000 omega____ theta____ kappa____ phi______ frames - -17.2885 57.0000 -120.0000 42 #__ type_ start__ end____ width___ exp.time_ 2 omega -19.00 87.00 1.0000 1.8000 omega____ theta____ kappa____ phi______ frames - 19.9448 19.0000 120.0000 106 ; _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0243430000 _diffrn_orient_matrix_UB_12 0.0129620000 _diffrn_orient_matrix_UB_13 -0.0365327000 _diffrn_orient_matrix_UB_21 0.0828038000 _diffrn_orient_matrix_UB_22 0.0254398000 _diffrn_orient_matrix_UB_23 -0.0049561000 _diffrn_orient_matrix_UB_31 0.0375319000 _diffrn_orient_matrix_UB_32 -0.0480007000 _diffrn_orient_matrix_UB_33 -0.0126236000 _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 n/a _diffrn_source_voltage n/a _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 2100 _reflns_number_total 3246 _reflns_odcompleteness_completeness 99.66 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) ; _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 ; XL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; XS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 0.117 _refine_diff_density_min -0.121 _refine_diff_density_rms 0.029 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -10(7) _refine_ls_extinction_coef 0.012(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 219 _refine_ls_number_reflns 3246 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1014 _refine_ls_R_factor_gt 0.0645 _refine_ls_restrained_S_all 1.046 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0613P)^2^+0.0093P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1413 _refine_ls_wR_factor_ref 0.1717 _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 N1 N 0.4395(4) 0.6927(2) 0.18757(14) 0.0551(7) Uani 1 1 d . . . H1 H 0.5059 0.6377 0.1894 0.066 Uiso 1 1 calc R . . C1 C 0.3404(4) 0.7224(2) 0.12730(17) 0.0517(8) Uani 1 1 d . . . C2 C 0.2532(5) 0.8132(2) 0.14718(19) 0.0568(9) Uani 1 1 d . . . H2 H 0.1763 0.8514 0.1174 0.068 Uiso 1 1 calc R . . C3 C 0.3002(4) 0.8390(2) 0.22081(19) 0.0563(9) Uani 1 1 d . . . C4 C 0.4177(4) 0.7629(2) 0.24421(18) 0.0546(8) Uani 1 1 d . . . C5 C 0.3374(5) 0.6626(2) 0.05890(17) 0.0522(8) Uani 1 1 d . . . C6 C 0.4200(6) 0.5666(3) 0.0510(2) 0.0725(11) Uani 1 1 d . . . H6 H 0.4779 0.5369 0.0911 0.087 Uiso 1 1 calc R . . C7 C 0.4187(6) 0.5135(3) -0.0151(2) 0.0788(12) Uani 1 1 d . . . H7 H 0.4787 0.4498 -0.0194 0.095 Uiso 1 1 calc R . . C8 C 0.3298(6) 0.5535(3) -0.0747(2) 0.0772(12) Uani 1 1 d . . . H8 H 0.3276 0.5175 -0.1192 0.093 Uiso 1 1 calc R . . C9 C 0.2453(6) 0.6470(3) -0.0669(2) 0.0834(12) Uani 1 1 d . . . H9 H 0.1837 0.6750 -0.1067 0.100 Uiso 1 1 calc R . . C10 C 0.2484(6) 0.7014(3) -0.0016(2) 0.0754(12) Uani 1 1 d . . . H10 H 0.1896 0.7656 0.0018 0.090 Uiso 1 1 calc R . . C11 C 0.2308(5) 0.9294(3) 0.2633(2) 0.0591(9) Uani 1 1 d . . . C12 C 0.1727(5) 1.0192(3) 0.2270(2) 0.0722(11) Uani 1 1 d . . . H12 H 0.1817 1.0230 0.1761 0.087 Uiso 1 1 calc R . . C13 C 0.1009(6) 1.1038(3) 0.2660(3) 0.0850(13) Uani 1 1 d . . . H13 H 0.0602 1.1627 0.2408 0.102 Uiso 1 1 calc R . . C14 C 0.0901(6) 1.1005(3) 0.3406(3) 0.0865(13) Uani 1 1 d . . . H14 H 0.0460 1.1580 0.3664 0.104 Uiso 1 1 calc R . . C15 C 0.1447(6) 1.0121(3) 0.3775(3) 0.0878(13) Uani 1 1 d . . . H15 H 0.1341 1.0091 0.4284 0.105 Uiso 1 1 calc R . . C16 C 0.2153(6) 0.9273(3) 0.3396(2) 0.0754(11) Uani 1 1 d . . . H16 H 0.2529 0.8682 0.3654 0.091 Uiso 1 1 calc R . . C17 C 0.5146(5) 0.7472(3) 0.31446(18) 0.0596(9) Uani 1 1 d . . . C18 C 0.4652(7) 0.6645(3) 0.3597(2) 0.0820(12) Uani 1 1 d . . . H18 H 0.3727 0.6207 0.3452 0.098 Uiso 1 1 calc R . . C19 C 0.5495(8) 0.6456(4) 0.4253(2) 0.0994(15) Uani 1 1 d . . . H19 H 0.5141 0.5902 0.4552 0.119 Uiso 1 1 calc R . . C20 C 0.6873(7) 0.7101(4) 0.4458(2) 0.0899(14) Uani 1 1 d . . . H20 H 0.7451 0.6985 0.4902 0.108 Uiso 1 1 calc R . . C21 C 0.7403(6) 0.7914(3) 0.4014(2) 0.0822(12) Uani 1 1 d . . . H21 H 0.8344 0.8338 0.4161 0.099 Uiso 1 1 calc R . . C22 C 0.6563(5) 0.8119(3) 0.33470(18) 0.0626(9) Uani 1 1 d . . . C23 C 0.7189(6) 0.8970(3) 0.2860(2) 0.0844(13) Uani 1 1 d . . . H23A H 0.7944 0.8680 0.2487 0.127 Uiso 1 1 calc R . . H23B H 0.7841 0.9476 0.3143 0.127 Uiso 1 1 calc R . . H23C H 0.6188 0.9306 0.2634 0.127 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 N1 0.0466(16) 0.0583(14) 0.0603(15) 0.0043(14) -0.0025(14) 0.0036(13) C1 0.0392(18) 0.0609(19) 0.0549(18) 0.0053(15) -0.0010(17) 0.0009(17) C2 0.0472(19) 0.0599(19) 0.063(2) 0.0050(17) -0.0084(18) 0.0018(18) C3 0.0410(18) 0.0609(19) 0.067(2) 0.0012(17) -0.0054(17) -0.0045(17) C4 0.0487(19) 0.0577(18) 0.0576(18) 0.0009(16) -0.0044(17) -0.0033(17) C5 0.0419(18) 0.0608(18) 0.0540(18) 0.0068(15) -0.0023(16) -0.0054(17) C6 0.085(3) 0.068(2) 0.065(2) 0.0039(19) -0.005(2) 0.009(2) C7 0.094(3) 0.066(2) 0.076(3) -0.002(2) 0.005(3) 0.011(2) C8 0.081(3) 0.084(3) 0.066(2) -0.007(2) -0.002(3) -0.013(3) C9 0.087(3) 0.101(3) 0.062(2) -0.004(2) -0.016(2) 0.009(3) C10 0.075(3) 0.086(2) 0.066(2) -0.002(2) -0.017(2) 0.025(2) C11 0.0435(19) 0.060(2) 0.074(2) -0.0030(18) -0.0039(19) -0.0062(18) C12 0.066(3) 0.063(2) 0.088(3) -0.001(2) 0.014(2) -0.006(2) C13 0.072(3) 0.059(2) 0.125(4) 0.003(2) 0.004(3) -0.004(2) C14 0.058(3) 0.081(3) 0.120(4) -0.030(3) 0.016(3) -0.006(2) C15 0.073(3) 0.108(3) 0.083(3) -0.024(3) 0.003(3) 0.009(3) C16 0.067(3) 0.087(3) 0.072(2) -0.007(2) 0.000(2) 0.015(2) C17 0.057(2) 0.066(2) 0.0556(19) 0.0008(17) -0.0045(19) 0.0013(19) C18 0.084(3) 0.093(3) 0.069(2) 0.017(2) -0.004(2) 0.004(3) C19 0.113(4) 0.107(3) 0.078(3) 0.027(3) 0.002(3) 0.004(3) C20 0.095(4) 0.114(3) 0.061(2) 0.009(2) -0.014(3) 0.019(3) C21 0.085(3) 0.098(3) 0.063(2) -0.008(2) -0.015(2) 0.005(3) C22 0.060(2) 0.068(2) 0.0598(19) -0.0029(17) -0.0022(19) 0.003(2) C23 0.075(3) 0.094(3) 0.084(3) 0.000(2) -0.015(2) -0.017(2) _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 N1 H1 0.8600 . ? N1 C1 1.379(4) . ? N1 C4 1.373(4) . ? C1 C2 1.376(4) . ? C1 C5 1.458(4) . ? C2 H2 0.9300 . ? C2 C3 1.424(4) . ? C3 C4 1.379(4) . ? C3 C11 1.480(5) . ? C4 C17 1.485(4) . ? C5 C6 1.377(4) . ? C5 C10 1.381(4) . ? C6 H6 0.9300 . ? C6 C7 1.380(5) . ? C7 H7 0.9300 . ? C7 C8 1.371(5) . ? C8 H8 0.9300 . ? C8 C9 1.355(5) . ? C9 H9 0.9300 . ? C9 C10 1.375(5) . ? C10 H10 0.9300 . ? C11 C12 1.390(5) . ? C11 C16 1.392(5) . ? C12 H12 0.9300 . ? C12 C13 1.397(5) . ? C13 H13 0.9300 . ? C13 C14 1.360(6) . ? C14 H14 0.9300 . ? C14 C15 1.372(6) . ? C15 H15 0.9300 . ? C15 C16 1.386(5) . ? C16 H16 0.9300 . ? C17 C18 1.386(5) . ? C17 C22 1.397(5) . ? C18 H18 0.9300 . ? C18 C19 1.373(6) . ? C19 H19 0.9300 . ? C19 C20 1.375(6) . ? C20 H20 0.9300 . ? C20 C21 1.372(6) . ? C21 H21 0.9300 . ? C21 C22 1.392(5) . ? C22 C23 1.475(5) . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 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 C1 N1 H1 124.6 . . ? C4 N1 H1 124.6 . . ? C4 N1 C1 110.7(3) . . ? N1 C1 C5 122.9(3) . . ? C2 C1 N1 106.2(3) . . ? C2 C1 C5 130.8(3) . . ? C1 C2 H2 125.6 . . ? C1 C2 C3 108.8(3) . . ? C3 C2 H2 125.6 . . ? C2 C3 C11 125.6(3) . . ? C4 C3 C2 106.8(3) . . ? C4 C3 C11 127.6(3) . . ? N1 C4 C3 107.5(3) . . ? N1 C4 C17 120.0(3) . . ? C3 C4 C17 132.5(3) . . ? C6 C5 C1 122.9(3) . . ? C6 C5 C10 117.0(3) . . ? C10 C5 C1 120.1(3) . . ? C5 C6 H6 119.3 . . ? C5 C6 C7 121.4(4) . . ? C7 C6 H6 119.3 . . ? C6 C7 H7 119.6 . . ? C8 C7 C6 120.7(4) . . ? C8 C7 H7 119.6 . . ? C7 C8 H8 120.9 . . ? C9 C8 C7 118.2(4) . . ? C9 C8 H8 120.9 . . ? C8 C9 H9 119.2 . . ? C8 C9 C10 121.5(4) . . ? C10 C9 H9 119.2 . . ? C5 C10 H10 119.4 . . ? C9 C10 C5 121.2(4) . . ? C9 C10 H10 119.4 . . ? C12 C11 C3 120.0(3) . . ? C12 C11 C16 117.6(3) . . ? C16 C11 C3 122.4(3) . . ? C11 C12 H12 119.6 . . ? C11 C12 C13 120.9(4) . . ? C13 C12 H12 119.6 . . ? C12 C13 H13 119.8 . . ? C14 C13 C12 120.4(4) . . ? C14 C13 H13 119.8 . . ? C13 C14 H14 120.1 . . ? C13 C14 C15 119.8(4) . . ? C15 C14 H14 120.1 . . ? C14 C15 H15 119.7 . . ? C14 C15 C16 120.5(4) . . ? C16 C15 H15 119.7 . . ? C11 C16 H16 119.5 . . ? C15 C16 C11 120.9(4) . . ? C15 C16 H16 119.5 . . ? C18 C17 C4 118.7(3) . . ? C18 C17 C22 119.7(3) . . ? C22 C17 C4 121.6(3) . . ? C17 C18 H18 119.2 . . ? C19 C18 C17 121.6(5) . . ? C19 C18 H18 119.2 . . ? C18 C19 H19 120.6 . . ? C18 C19 C20 118.8(4) . . ? C20 C19 H19 120.6 . . ? C19 C20 H20 119.7 . . ? C21 C20 C19 120.6(4) . . ? C21 C20 H20 119.7 . . ? C20 C21 H21 119.3 . . ? C20 C21 C22 121.4(4) . . ? C22 C21 H21 119.3 . . ? C17 C22 C23 121.2(3) . . ? C21 C22 C17 117.9(3) . . ? C21 C22 C23 121.0(4) . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23B 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 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 N1 C1 C2 C3 0.0(4) . . . . ? N1 C1 C5 C6 6.2(5) . . . . ? N1 C1 C5 C10 -174.1(3) . . . . ? N1 C4 C17 C18 -70.3(4) . . . . ? N1 C4 C17 C22 107.9(4) . . . . ? C1 N1 C4 C3 0.9(4) . . . . ? C1 N1 C4 C17 -179.0(3) . . . . ? C1 C2 C3 C4 0.6(4) . . . . ? C1 C2 C3 C11 -178.2(3) . . . . ? C1 C5 C6 C7 -178.2(4) . . . . ? C1 C5 C10 C9 179.3(4) . . . . ? C2 C1 C5 C6 -173.2(4) . . . . ? C2 C1 C5 C10 6.6(6) . . . . ? C2 C3 C4 N1 -0.8(4) . . . . ? C2 C3 C4 C17 179.0(4) . . . . ? C2 C3 C11 C12 -26.8(5) . . . . ? C2 C3 C11 C16 151.0(4) . . . . ? C3 C4 C17 C18 109.8(4) . . . . ? C3 C4 C17 C22 -72.0(5) . . . . ? C3 C11 C12 C13 177.7(3) . . . . ? C3 C11 C16 C15 -178.0(3) . . . . ? C4 N1 C1 C2 -0.5(4) . . . . ? C4 N1 C1 C5 -180.0(3) . . . . ? C4 C3 C11 C12 154.7(3) . . . . ? C4 C3 C11 C16 -27.5(6) . . . . ? C4 C17 C18 C19 179.9(4) . . . . ? C4 C17 C22 C21 -179.7(3) . . . . ? C4 C17 C22 C23 -1.7(5) . . . . ? C5 C1 C2 C3 179.4(3) . . . . ? C5 C6 C7 C8 -2.0(7) . . . . ? C6 C5 C10 C9 -0.9(6) . . . . ? C6 C7 C8 C9 0.7(7) . . . . ? C7 C8 C9 C10 0.4(7) . . . . ? C8 C9 C10 C5 -0.3(7) . . . . ? C10 C5 C6 C7 2.1(6) . . . . ? C11 C3 C4 N1 177.9(3) . . . . ? C11 C3 C4 C17 -2.2(6) . . . . ? C11 C12 C13 C14 1.4(6) . . . . ? C12 C11 C16 C15 -0.1(6) . . . . ? C12 C13 C14 C15 -2.2(7) . . . . ? C13 C14 C15 C16 1.8(7) . . . . ? C14 C15 C16 C11 -0.7(7) . . . . ? C16 C11 C12 C13 -0.2(6) . . . . ? C17 C18 C19 C20 -0.6(7) . . . . ? C18 C17 C22 C21 -1.5(5) . . . . ? C18 C17 C22 C23 176.6(4) . . . . ? C18 C19 C20 C21 -0.4(7) . . . . ? C19 C20 C21 C22 0.5(7) . . . . ? C20 C21 C22 C17 0.5(6) . . . . ? C20 C21 C22 C23 -177.6(4) . . . . ? C22 C17 C18 C19 1.6(6) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 957208' ####################################################################### # # 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_4ah _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H15 N S' _chemical_formula_weight 301.39 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' S S 0.1246 0.1234 '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, y+1/2, -z' _cell_length_a 6.1065(4) _cell_length_b 7.7764(6) _cell_length_c 16.7309(10) _cell_angle_alpha 90.00 _cell_angle_beta 99.353(6) _cell_angle_gamma 90.00 _cell_volume 783.93(9) _cell_formula_units_Z 2 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.277 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 316 _exptl_absorpt_coefficient_mu 0.202 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9419 _exptl_absorpt_correction_T_max 0.9608 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(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 3014 _diffrn_reflns_av_R_equivalents 0.0174 _diffrn_reflns_av_sigmaI/netI 0.0443 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.38 _diffrn_reflns_theta_max 26.37 _reflns_number_total 2473 _reflns_number_gt 1995 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.1000P)^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 none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.23(11) _refine_ls_number_reflns 2473 _refine_ls_number_parameters 199 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0564 _refine_ls_R_factor_gt 0.0429 _refine_ls_wR_factor_ref 0.1325 _refine_ls_wR_factor_gt 0.1180 _refine_ls_goodness_of_fit_ref 0.843 _refine_ls_restrained_S_all 0.843 _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 S1 S 0.33404(15) 0.38815(16) 0.37823(5) 0.0677(3) Uani 1 1 d . . . N1 N -0.1625(4) 0.1706(4) 0.16221(14) 0.0416(6) Uani 1 1 d . . . H1 H -0.2734 0.1010 0.1553 0.050 Uiso 1 1 calc R . . C1 C -0.0103(4) 0.1834(4) 0.23235(16) 0.0384(6) Uani 1 1 d . . . C2 C 0.1389(4) 0.3113(4) 0.21867(16) 0.0408(6) Uani 1 1 d . . . C3 C 0.0717(4) 0.3714(5) 0.13883(15) 0.0431(7) Uani 1 1 d . . . H3 H 0.1421 0.4569 0.1135 0.052 Uiso 1 1 calc R . . C4 C -0.1135(4) 0.2835(4) 0.10490(16) 0.0389(6) Uani 1 1 d . . . C5 C -0.2435(4) 0.2941(4) 0.02307(16) 0.0410(7) Uani 1 1 d . . . C6 C -0.4551(5) 0.2268(5) 0.00422(19) 0.0527(8) Uani 1 1 d . . . H6 H -0.5208 0.1755 0.0446 0.063 Uiso 1 1 calc R . . C7 C -0.5706(6) 0.2349(5) -0.0742(2) 0.0574(9) Uani 1 1 d . . . H7 H -0.7109 0.1859 -0.0864 0.069 Uiso 1 1 calc R . . C8 C -0.4778(6) 0.3156(5) -0.13403(18) 0.0567(9) Uani 1 1 d . . . H8 H -0.5559 0.3232 -0.1865 0.068 Uiso 1 1 calc R . . C9 C -0.2698(6) 0.3842(7) -0.11531(18) 0.0633(9) Uani 1 1 d . . . H9 H -0.2059 0.4376 -0.1556 0.076 Uiso 1 1 calc R . . C10 C -0.1541(5) 0.3756(6) -0.03834(17) 0.0528(8) Uani 1 1 d . . . H10 H -0.0137 0.4248 -0.0268 0.063 Uiso 1 1 calc R . . C11 C -0.0184(4) 0.0714(4) 0.30339(16) 0.0390(6) Uani 1 1 d . . . C12 C -0.2032(5) 0.0670(5) 0.3409(2) 0.0494(8) Uani 1 1 d . . . H12 H -0.3262 0.1337 0.3206 0.059 Uiso 1 1 calc R . . C13 C -0.2081(5) -0.0350(6) 0.4079(2) 0.0614(9) Uani 1 1 d . . . H13 H -0.3332 -0.0359 0.4330 0.074 Uiso 1 1 calc R . . C14 C -0.0278(5) -0.1353(5) 0.43749(19) 0.0601(9) Uani 1 1 d . . . H14 H -0.0299 -0.2028 0.4833 0.072 Uiso 1 1 calc R . . C15 C 0.1537(5) -0.1359(5) 0.3999(2) 0.0576(9) Uani 1 1 d . . . H15 H 0.2741 -0.2061 0.4192 0.069 Uiso 1 1 calc R . . C16 C 0.1596(5) -0.0337(5) 0.33375(19) 0.0494(8) Uani 1 1 d . . . H16 H 0.2849 -0.0346 0.3087 0.059 Uiso 1 1 calc R . . C17 C 0.3268(4) 0.3802(5) 0.27474(16) 0.0417(6) Uani 1 1 d . . . C18 C 0.5143(5) 0.4559(4) 0.25485(19) 0.0510(8) Uani 1 1 d . . . H18 H 0.5441 0.4643 0.2022 0.061 Uiso 1 1 calc R . . C19 C 0.6571(6) 0.5198(5) 0.3239(3) 0.0677(11) Uani 1 1 d . . . H19 H 0.7907 0.5751 0.3211 0.081 Uiso 1 1 calc R . . C20 C 0.5812(6) 0.4928(6) 0.3930(2) 0.0718(11) Uani 1 1 d . . . H20 H 0.6550 0.5272 0.4434 0.086 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 S1 0.0699(6) 0.0860(7) 0.0444(4) -0.0120(5) 0.0010(4) -0.0070(6) N1 0.0387(11) 0.0495(15) 0.0356(12) 0.0038(12) 0.0029(9) -0.0044(12) C1 0.0388(13) 0.0446(16) 0.0317(13) -0.0003(14) 0.0052(10) 0.0033(14) C2 0.0445(14) 0.0455(16) 0.0319(13) 0.0005(14) 0.0051(11) 0.0016(14) C3 0.0458(14) 0.0480(16) 0.0357(14) 0.0033(16) 0.0073(11) -0.0053(16) C4 0.0427(14) 0.0434(16) 0.0311(14) 0.0054(13) 0.0074(11) 0.0008(14) C5 0.0432(14) 0.0441(16) 0.0356(15) 0.0011(14) 0.0057(11) 0.0045(14) C6 0.0540(18) 0.056(2) 0.0450(16) 0.0090(17) -0.0002(14) -0.0076(16) C7 0.0559(18) 0.056(2) 0.055(2) -0.0001(18) -0.0084(15) -0.0044(17) C8 0.078(2) 0.050(2) 0.0353(16) -0.0045(16) -0.0112(15) 0.0109(18) C9 0.078(2) 0.074(2) 0.0370(16) 0.011(2) 0.0085(14) -0.002(2) C10 0.0551(17) 0.062(2) 0.0416(15) 0.000(2) 0.0104(12) -0.0074(19) C11 0.0427(14) 0.0413(15) 0.0317(14) -0.0024(14) 0.0022(11) -0.0036(14) C12 0.0425(15) 0.056(2) 0.0496(18) 0.0137(17) 0.0089(13) 0.0029(15) C13 0.0536(18) 0.075(2) 0.0569(19) 0.018(2) 0.0127(15) -0.0016(19) C14 0.070(2) 0.065(2) 0.0415(16) 0.0151(19) -0.0025(14) -0.017(2) C15 0.0588(18) 0.059(2) 0.0507(18) 0.0093(19) -0.0045(14) 0.0074(19) C16 0.0423(15) 0.062(2) 0.0428(16) 0.0063(17) 0.0050(12) 0.0052(16) C17 0.0434(14) 0.0391(14) 0.0402(14) -0.0010(16) -0.0008(11) 0.0014(15) C18 0.0517(16) 0.0463(18) 0.0523(18) 0.0090(17) 0.0003(14) -0.0036(16) C19 0.0547(19) 0.054(2) 0.088(3) 0.007(2) -0.0078(18) -0.0116(17) C20 0.073(2) 0.069(3) 0.063(2) -0.013(2) -0.0196(19) -0.002(2) _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 S1 C20 1.697(4) . ? S1 C17 1.726(3) . ? N1 C4 1.369(4) . ? N1 C1 1.377(3) . ? N1 H1 0.8600 . ? C1 C2 1.393(4) . ? C1 C11 1.481(4) . ? C2 C3 1.412(4) . ? C2 C17 1.461(4) . ? C3 C4 1.364(4) . ? C3 H3 0.9300 . ? C4 C5 1.469(4) . ? C5 C6 1.382(4) . ? C5 C10 1.392(4) . ? C6 C7 1.386(4) . ? C6 H6 0.9300 . ? C7 C8 1.379(5) . ? C7 H7 0.9300 . ? C8 C9 1.367(5) . ? C8 H8 0.9300 . ? C9 C10 1.366(4) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 C12 1.377(4) . ? C11 C16 1.389(4) . ? C12 C13 1.378(5) . ? C12 H12 0.9300 . ? C13 C14 1.375(5) . ? C13 H13 0.9300 . ? C14 C15 1.360(5) . ? C14 H14 0.9300 . ? C15 C16 1.368(5) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 C18 1.376(4) . ? C18 C19 1.419(5) . ? C18 H18 0.9300 . ? C19 C20 1.330(6) . ? C19 H19 0.9300 . ? C20 H20 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 C20 S1 C17 92.29(18) . . ? C4 N1 C1 110.9(2) . . ? C4 N1 H1 124.6 . . ? C1 N1 H1 124.6 . . ? N1 C1 C2 106.3(2) . . ? N1 C1 C11 122.4(3) . . ? C2 C1 C11 131.3(2) . . ? C1 C2 C3 107.1(3) . . ? C1 C2 C17 128.5(3) . . ? C3 C2 C17 124.3(3) . . ? C4 C3 C2 108.8(3) . . ? C4 C3 H3 125.6 . . ? C2 C3 H3 125.6 . . ? C3 C4 N1 106.9(2) . . ? C3 C4 C5 130.2(3) . . ? N1 C4 C5 122.8(3) . . ? C6 C5 C10 117.9(3) . . ? C6 C5 C4 122.3(3) . . ? C10 C5 C4 119.7(3) . . ? C5 C6 C7 120.8(3) . . ? C5 C6 H6 119.6 . . ? C7 C6 H6 119.6 . . ? C8 C7 C6 120.2(3) . . ? C8 C7 H7 119.9 . . ? C6 C7 H7 119.9 . . ? C9 C8 C7 119.2(3) . . ? C9 C8 H8 120.4 . . ? C7 C8 H8 120.4 . . ? C10 C9 C8 121.1(3) . . ? C10 C9 H9 119.5 . . ? C8 C9 H9 119.5 . . ? C9 C10 C5 120.9(3) . . ? C9 C10 H10 119.6 . . ? C5 C10 H10 119.6 . . ? C12 C11 C16 118.0(3) . . ? C12 C11 C1 121.1(3) . . ? C16 C11 C1 120.9(3) . . ? C11 C12 C13 120.8(3) . . ? C11 C12 H12 119.6 . . ? C13 C12 H12 119.6 . . ? C14 C13 C12 119.9(3) . . ? C14 C13 H13 120.1 . . ? C12 C13 H13 120.1 . . ? C15 C14 C13 120.0(3) . . ? C15 C14 H14 120.0 . . ? C13 C14 H14 120.0 . . ? C14 C15 C16 120.2(3) . . ? C14 C15 H15 119.9 . . ? C16 C15 H15 119.9 . . ? C15 C16 C11 121.1(3) . . ? C15 C16 H16 119.5 . . ? C11 C16 H16 119.5 . . ? C18 C17 C2 126.8(3) . . ? C18 C17 S1 109.9(2) . . ? C2 C17 S1 123.2(2) . . ? C17 C18 C19 112.3(3) . . ? C17 C18 H18 123.9 . . ? C19 C18 H18 123.9 . . ? C20 C19 C18 113.4(3) . . ? C20 C19 H19 123.3 . . ? C18 C19 H19 123.3 . . ? C19 C20 S1 112.1(3) . . ? C19 C20 H20 123.9 . . ? S1 C20 H20 123.9 . . ? 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 C4 N1 C1 C2 0.7(3) . . . . ? C4 N1 C1 C11 -177.7(3) . . . . ? N1 C1 C2 C3 -0.6(3) . . . . ? C11 C1 C2 C3 177.6(3) . . . . ? N1 C1 C2 C17 177.3(3) . . . . ? C11 C1 C2 C17 -4.6(5) . . . . ? C1 C2 C3 C4 0.3(4) . . . . ? C17 C2 C3 C4 -177.7(3) . . . . ? C2 C3 C4 N1 0.1(4) . . . . ? C2 C3 C4 C5 -178.1(3) . . . . ? C1 N1 C4 C3 -0.5(3) . . . . ? C1 N1 C4 C5 177.9(3) . . . . ? C3 C4 C5 C6 -164.1(3) . . . . ? N1 C4 C5 C6 17.8(5) . . . . ? C3 C4 C5 C10 15.3(5) . . . . ? N1 C4 C5 C10 -162.7(3) . . . . ? C10 C5 C6 C7 2.3(5) . . . . ? C4 C5 C6 C7 -178.2(3) . . . . ? C5 C6 C7 C8 -2.1(6) . . . . ? C6 C7 C8 C9 1.2(6) . . . . ? C7 C8 C9 C10 -0.7(6) . . . . ? C8 C9 C10 C5 1.0(7) . . . . ? C6 C5 C10 C9 -1.8(6) . . . . ? C4 C5 C10 C9 178.7(4) . . . . ? N1 C1 C11 C12 -58.3(4) . . . . ? C2 C1 C11 C12 123.8(4) . . . . ? N1 C1 C11 C16 121.1(3) . . . . ? C2 C1 C11 C16 -56.9(5) . . . . ? C16 C11 C12 C13 1.9(5) . . . . ? C1 C11 C12 C13 -178.7(3) . . . . ? C11 C12 C13 C14 -0.7(6) . . . . ? C12 C13 C14 C15 -1.1(6) . . . . ? C13 C14 C15 C16 1.6(6) . . . . ? C14 C15 C16 C11 -0.4(5) . . . . ? C12 C11 C16 C15 -1.3(5) . . . . ? C1 C11 C16 C15 179.3(3) . . . . ? C1 C2 C17 C18 154.4(3) . . . . ? C3 C2 C17 C18 -28.1(5) . . . . ? C1 C2 C17 S1 -29.7(5) . . . . ? C3 C2 C17 S1 147.8(3) . . . . ? C20 S1 C17 C18 0.6(3) . . . . ? C20 S1 C17 C2 -175.9(3) . . . . ? C2 C17 C18 C19 175.7(3) . . . . ? S1 C17 C18 C19 -0.6(4) . . . . ? C17 C18 C19 C20 0.3(5) . . . . ? C18 C19 C20 S1 0.2(5) . . . . ? C17 S1 C20 C19 -0.5(4) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.166 _refine_diff_density_min -0.214 _refine_diff_density_rms 0.036 _database_code_depnum_ccdc_archive 'CCDC 957400'