Supplementary Material (ESI) for Perkin Transactions This journal is © The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge 188 _publ_requested_journal 'Perkin Transactions 2' loop_ _publ_author_name 'Karlsen, Hege' 'Kolsaker, Per' 'Romming, Christian' 'Uggerud, Einar' _publ_contact_author_name 'Prof Per Kolsaker' _publ_contact_author_address ; Department of Chemistry University of Oslo P OBox 1033 Blindern N-0315 Oslo NORWAY ; _publ_contact_author_email 'PER.KOLSAKER@KJEMI.UIO.NO' _publ_section_title ; The analogy between C==O and C(CN)2. Part 2: Structural Properties of N,N-Dialkylaminobenzamides and The Analogously Substituted 2-(Phenylmethylene)propanedinitriles ; data_4a _database_code_CSD 168509 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-(N,N-Dimethylamino-phenyl-methylene)propanedinitrile ; _chemical_name_common ? _chemical_melting_point '121-122 degC' _chemical_formula_moiety ? _chemical_formula_sum 'C12 H11 N3' _chemical_formula_weight 197.24 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' _symmetry_cell_setting ? _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.1388(5) _cell_length_b 7.9552(5) _cell_length_c 9.4073(6) _cell_angle_alpha 90.00 _cell_angle_beta 96.849(3) _cell_angle_gamma 90.00 _cell_volume 530.43(6) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.35 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.235 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 208 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type SADABS _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 5791 _diffrn_reflns_av_R_equivalents 0.0268 _diffrn_reflns_av_sigmaI/netI 0.0235 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 5.13 _diffrn_reflns_theta_max 26.37 _reflns_number_total 2096 _reflns_number_gt 1925 _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^)+(0.0450P)^2^+0.0300P] 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 2096 _refine_ls_number_parameters 180 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0334 _refine_ls_R_factor_gt 0.0286 _refine_ls_wR_factor_ref 0.0724 _refine_ls_wR_factor_gt 0.0696 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.028 _refine_ls_shift/su_mean 0.003 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 1.35742(16) 0.34145(16) 0.23251(14) 0.0370(3) Uani 1 1 d . . . N2 N 0.81534(17) 0.53419(17) 0.07616(14) 0.0391(3) Uani 1 1 d . . . N3 N 0.75742(14) 0.06491(15) 0.16702(12) 0.0290(3) Uani 1 1 d . . . C1 C 1.00137(17) 0.27612(16) 0.18156(14) 0.0267(3) Uani 1 1 d . . . C2 C 1.19963(18) 0.30836(17) 0.21129(15) 0.0282(3) Uani 1 1 d . . . C3 C 0.89455(18) 0.41589(18) 0.12108(15) 0.0294(3) Uani 1 1 d . . . C4 C 0.92814(17) 0.12160(16) 0.21964(14) 0.0253(3) Uani 1 1 d . . . C5 C 1.05243(17) 0.01059(17) 0.31790(14) 0.0265(3) Uani 1 1 d . . . C6 C 1.09414(18) -0.15183(17) 0.27488(15) 0.0299(3) Uani 1 1 d . . . H6 H 1.030(2) -0.191(2) 0.1854(19) 0.035(4) Uiso 1 1 d . . . C7 C 1.2229(2) -0.24993(19) 0.36018(17) 0.0347(3) Uani 1 1 d . . . H7 H 1.258(2) -0.362(2) 0.3287(17) 0.033(4) Uiso 1 1 d . . . C8 C 1.30879(19) -0.1883(2) 0.48982(16) 0.0356(3) Uani 1 1 d . . . H8 H 1.397(2) -0.256(2) 0.5511(18) 0.038(4) Uiso 1 1 d . . . C9 C 1.2657(2) -0.02831(19) 0.53522(17) 0.0351(3) Uani 1 1 d . . . H9 H 1.324(2) 0.015(2) 0.6303(19) 0.039(4) Uiso 1 1 d . . . C10 C 1.13891(18) 0.07177(19) 0.44899(15) 0.0306(3) Uani 1 1 d . . . H10 H 1.109(2) 0.177(2) 0.4807(18) 0.036(4) Uiso 1 1 d . . . C11 C 0.6506(2) 0.1367(2) 0.03871(17) 0.0340(3) Uani 1 1 d . . . H11A H 0.576(2) 0.050(3) -0.0047(19) 0.047(5) Uiso 1 1 d . . . H11B H 0.741(3) 0.174(2) -0.0269(19) 0.039(4) Uiso 1 1 d . . . H11C H 0.567(3) 0.225(2) 0.060(2) 0.044(5) Uiso 1 1 d . . . C12 C 0.6577(2) -0.0673(2) 0.23726(19) 0.0394(4) Uani 1 1 d . . . H12A H 0.721(2) -0.084(3) 0.334(2) 0.044(5) Uiso 1 1 d . . . H12B H 0.664(3) -0.169(3) 0.181(2) 0.055(6) Uiso 1 1 d . . . H12C H 0.522(3) -0.036(2) 0.240(2) 0.051(5) 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 N1 0.0306(6) 0.0339(7) 0.0454(7) -0.0004(5) 0.0009(5) -0.0041(5) N2 0.0365(6) 0.0324(7) 0.0467(7) 0.0043(6) -0.0021(5) 0.0025(5) N3 0.0248(5) 0.0298(6) 0.0322(6) -0.0008(5) 0.0020(4) -0.0020(4) C1 0.0253(6) 0.0269(7) 0.0277(6) -0.0025(5) 0.0020(5) 0.0006(5) C2 0.0308(7) 0.0231(6) 0.0306(6) -0.0019(5) 0.0024(5) 0.0010(5) C3 0.0277(6) 0.0308(7) 0.0299(7) -0.0019(6) 0.0037(5) -0.0032(5) C4 0.0249(6) 0.0263(6) 0.0250(6) -0.0056(5) 0.0043(5) 0.0010(5) C5 0.0235(6) 0.0285(7) 0.0280(6) 0.0006(5) 0.0050(5) -0.0019(5) C6 0.0310(6) 0.0273(7) 0.0316(7) -0.0003(5) 0.0042(6) -0.0035(5) C7 0.0361(7) 0.0260(7) 0.0430(8) 0.0027(6) 0.0081(6) 0.0007(6) C8 0.0315(7) 0.0362(8) 0.0389(8) 0.0119(7) 0.0030(6) 0.0028(6) C9 0.0339(7) 0.0421(9) 0.0289(7) 0.0020(6) 0.0023(6) -0.0030(6) C10 0.0306(7) 0.0310(8) 0.0303(7) -0.0035(6) 0.0043(5) 0.0010(6) C11 0.0271(7) 0.0370(8) 0.0362(8) -0.0049(6) -0.0037(6) -0.0017(6) C12 0.0304(8) 0.0378(9) 0.0501(10) 0.0031(8) 0.0052(7) -0.0075(6) _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 C2 1.1508(17) . ? N2 C3 1.152(2) . ? N3 C4 1.3379(16) . ? N3 C11 1.4646(18) . ? N3 C12 1.4703(19) . ? C1 C4 1.3990(19) . ? C1 C3 1.4276(19) . ? C1 C2 1.4327(17) . ? C4 C5 1.4920(18) . ? C5 C10 1.3990(18) . ? C5 C6 1.3967(19) . ? C6 C7 1.386(2) . ? C6 H6 0.961(18) . ? C7 C8 1.387(2) . ? C7 H7 0.982(18) . ? C8 C9 1.389(2) . ? C8 H8 0.966(18) . ? C9 C10 1.391(2) . ? C9 H9 1.002(17) . ? C10 H10 0.922(18) . ? C11 H11A 0.94(2) . ? C11 H11B 0.990(19) . ? C11 H11C 0.959(19) . ? C12 H12A 0.974(19) . ? C12 H12B 0.97(2) . ? C12 H12C 1.004(19) . ? 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 C4 N3 C11 122.36(12) . . ? C4 N3 C12 122.92(12) . . ? C11 N3 C12 114.63(11) . . ? C4 C1 C3 126.03(11) . . ? C4 C1 C2 119.86(11) . . ? C3 C1 C2 113.99(12) . . ? N1 C2 C1 176.87(15) . . ? N2 C3 C1 176.37(15) . . ? N3 C4 C1 123.58(12) . . ? N3 C4 C5 118.55(11) . . ? C1 C4 C5 117.77(11) . . ? C10 C5 C6 119.36(12) . . ? C10 C5 C4 120.50(12) . . ? C6 C5 C4 119.98(11) . . ? C7 C6 C5 120.17(13) . . ? C7 C6 H6 122.5(11) . . ? C5 C6 H6 117.4(11) . . ? C8 C7 C6 120.20(14) . . ? C8 C7 H7 118.9(9) . . ? C6 C7 H7 120.9(9) . . ? C9 C8 C7 120.20(14) . . ? C9 C8 H8 118.8(10) . . ? C7 C8 H8 121.0(10) . . ? C8 C9 C10 119.85(14) . . ? C8 C9 H9 120.6(10) . . ? C10 C9 H9 119.6(10) . . ? C9 C10 C5 120.19(14) . . ? C9 C10 H10 119.3(10) . . ? C5 C10 H10 120.5(10) . . ? N3 C11 H11A 106.6(12) . . ? N3 C11 H11B 108.3(10) . . ? H11A C11 H11B 109.2(15) . . ? N3 C11 H11C 112.7(11) . . ? H11A C11 H11C 107.1(15) . . ? H11B C11 H11C 112.6(15) . . ? N3 C12 H12A 108.6(12) . . ? N3 C12 H12B 107.3(12) . . ? H12A C12 H12B 110.3(17) . . ? N3 C12 H12C 110.8(11) . . ? H12A C12 H12C 110.9(15) . . ? H12B C12 H12C 108.9(16) . . ? 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 C1 C2 N1 -179(100) . . . . ? C3 C1 C2 N1 -3(3) . . . . ? C4 C1 C3 N2 146(2) . . . . ? C2 C1 C3 N2 -30(2) . . . . ? C11 N3 C4 C1 16.1(2) . . . . ? C12 N3 C4 C1 -160.36(14) . . . . ? C11 N3 C4 C5 -160.25(12) . . . . ? C12 N3 C4 C5 23.27(19) . . . . ? C3 C1 C4 N3 20.7(2) . . . . ? C2 C1 C4 N3 -163.37(13) . . . . ? C3 C1 C4 C5 -162.86(12) . . . . ? C2 C1 C4 C5 13.02(18) . . . . ? N3 C4 C5 C10 -130.11(13) . . . . ? C1 C4 C5 C10 53.31(17) . . . . ? N3 C4 C5 C6 54.52(17) . . . . ? C1 C4 C5 C6 -122.06(13) . . . . ? C10 C5 C6 C7 -1.28(19) . . . . ? C4 C5 C6 C7 174.14(12) . . . . ? C5 C6 C7 C8 1.0(2) . . . . ? C6 C7 C8 C9 0.3(2) . . . . ? C7 C8 C9 C10 -1.3(2) . . . . ? C8 C9 C10 C5 1.1(2) . . . . ? C6 C5 C10 C9 0.23(19) . . . . ? C4 C5 C10 C9 -175.16(12) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.132 _refine_diff_density_min -0.121 _refine_diff_density_rms 0.028 #==END data_4b _database_code_CSD 168510 _audit_creation_method SHELXL _chemical_name_systematic ; 2-(N,N-diethylamino-phenyl-methylene)propanedinitrile ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C14 H15 N3' _chemical_formula_weight 225.29 _chemical_melting_point '96-97 degC' _chemical_compound_source ? 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' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.8830(2) _cell_length_b 14.4539(4) _cell_length_c 8.9153(2) _cell_angle_alpha 90.00 _cell_angle_beta 95.3630(10) _cell_angle_gamma 90.00 _cell_volume 1267.96(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.49 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.33 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.180 _exptl_crystal_density_method ? _exptl_crystal_F_000 480 _exptl_absorpt_coefficient_mu 0.072 _exptl_absorpt_correction_type SADABS _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17827 _diffrn_reflns_av_R_equivalents 0.0180 _diffrn_reflns_av_sigmaI/netI 0.0199 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 37.83 _reflns_number_total 6541 _reflns_number_observed 3849 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 2111 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w==1/[\s^2^(Fo^2^)+(0.0350P)^2^+0.2200P] 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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4430 _refine_ls_number_parameters 214 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0667 _refine_ls_R_factor_obs 0.0468 _refine_ls_wR_factor_all 0.1406 _refine_ls_wR_factor_obs 0.1067 _refine_ls_goodness_of_fit_all 1.131 _refine_ls_goodness_of_fit_obs 1.146 _refine_ls_restrained_S_all 1.497 _refine_ls_restrained_S_obs 1.146 _refine_ls_shift/esd_max -0.023 _refine_ls_shift/esd_mean 0.002 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group N1 N 0.23667(11) 0.36366(6) 0.61165(10) 0.0356(2) Uani 1 d . . N2 N -0.07879(11) 0.25787(8) 0.8550(2) 0.0440(2) Uani 1 d . . N3 N 0.16231(6) 0.04947(4) 0.75941(7) 0.01988(13) Uani 1 d . . C1 C 0.13857(7) 0.21713(5) 0.72793(8) 0.02100(14) Uani 1 d . . C2 C 0.19558(9) 0.29672(5) 0.66333(9) 0.02444(15) Uani 1 d . . C3 C 0.01738(9) 0.23631(6) 0.79738(11) 0.0294(2) Uani 1 d . . C4 C 0.20689(7) 0.13219(5) 0.72061(7) 0.01748(13) Uani 1 d . . C5 C 0.34381(7) 0.13787(5) 0.66224(8) 0.01785(13) Uani 1 d . . C6 C 0.35654(8) 0.12799(6) 0.50840(8) 0.02256(14) Uani 1 d . . H6A H 0.2821(24) 0.1149(16) 0.4463(26) 0.038(4) Uiso 1 d . . C7 C 0.48337(9) 0.13884(6) 0.45399(10) 0.0269(2) Uani 1 d . . H7A H 0.4914(23) 0.1346(15) 0.3600(28) 0.036(4) Uiso 1 d . . C8 C 0.59681(8) 0.16004(6) 0.55258(12) 0.0290(2) Uani 1 d . . H8A H 0.6801(25) 0.1703(17) 0.5148(28) 0.040(4) Uiso 1 d . . C9 C 0.58422(8) 0.16896(7) 0.70644(11) 0.0294(2) Uani 1 d . . H9A H 0.6555(28) 0.1829(19) 0.7689(30) 0.044(5) Uiso 1 d . . C10 C 0.45752(8) 0.15770(6) 0.76202(9) 0.02420(15) Uani 1 d . . H10A H 0.4473(20) 0.1675(14) 0.8587(24) 0.031(4) Uiso 1 d . . C11 C 0.02569(8) 0.03504(6) 0.80880(9) 0.02480(15) Uani 1 d . . H11A H 0.0072(20) 0.0807(13) 0.8812(22) 0.029(3) Uiso 1 d . . H11B H 0.0271(24) -0.0243(17) 0.8529(26) 0.039(4) Uiso 1 d . . C12 C -0.08389(9) 0.03480(8) 0.67685(12) 0.0326(2) Uani 1 d . . H12A H -0.1705(29) 0.0290(19) 0.7124(31) 0.046(5) Uiso 1 d . . H12B H -0.0656(28) -0.0187(20) 0.6196(32) 0.047(5) Uiso 1 d . . H12C H -0.0836(29) 0.0914(21) 0.6244(33) 0.047(5) Uiso 1 d . . C13 C 0.24475(9) -0.03528(5) 0.75152(9) 0.02468(15) Uani 1 d . . H13A H 0.3108(21) -0.0248(14) 0.6876(23) 0.031(4) Uiso 1 d . . H13B H 0.1852(22) -0.0817(15) 0.7105(25) 0.034(4) Uiso 1 d . . C14 C 0.30597(15) -0.06674(8) 0.90594(14) 0.0421(3) Uani 1 d . . H14A H 0.3506(38) -0.1212(26) 0.8935(42) 0.061(7) Uiso 1 d . . H14B H 0.2271(35) -0.0790(23) 0.9710(39) 0.057(6) Uiso 1 d . . H14C H 0.3642(34) -0.0205(24) 0.9601(38) 0.055(6) Uiso 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 N1 0.0519(5) 0.0225(3) 0.0322(4) 0.0047(3) 0.0027(3) -0.0005(3) N2 0.0333(4) 0.0367(4) 0.0645(6) -0.0034(4) 0.0168(4) 0.0096(3) N3 0.0211(2) 0.0180(2) 0.0209(3) 0.0010(2) 0.0040(2) 0.0001(2) C1 0.0210(3) 0.0188(3) 0.0232(3) 0.0010(2) 0.0019(2) 0.0034(2) C2 0.0305(3) 0.0195(3) 0.0227(3) 0.0010(2) -0.0008(2) 0.0034(2) C3 0.0254(3) 0.0249(3) 0.0381(4) -0.0013(3) 0.0047(3) 0.0062(3) C4 0.0183(2) 0.0176(3) 0.0163(2) 0.0000(2) 0.0005(2) 0.0009(2) C5 0.0174(2) 0.0173(2) 0.0188(3) 0.0005(2) 0.0016(2) 0.0008(2) C6 0.0220(3) 0.0266(3) 0.0191(3) -0.0004(2) 0.0022(2) 0.0009(2) C7 0.0264(3) 0.0304(4) 0.0250(3) 0.0016(3) 0.0085(3) 0.0040(3) C8 0.0205(3) 0.0295(4) 0.0378(4) 0.0018(3) 0.0082(3) 0.0024(3) C9 0.0180(3) 0.0343(4) 0.0354(4) -0.0029(3) -0.0005(3) -0.0013(3) C10 0.0200(3) 0.0290(3) 0.0229(3) -0.0024(2) -0.0015(2) -0.0001(2) C11 0.0259(3) 0.0255(3) 0.0243(3) 0.0029(2) 0.0093(2) -0.0016(2) C12 0.0230(3) 0.0394(5) 0.0358(4) -0.0037(3) 0.0044(3) -0.0077(3) C13 0.0306(3) 0.0164(3) 0.0277(3) -0.0007(2) 0.0066(3) 0.0025(2) C14 0.0542(6) 0.0329(5) 0.0380(5) 0.0051(4) -0.0020(4) 0.0193(4) _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 C2 1.1612(12) . ? N2 C3 1.1643(13) . ? N3 C4 1.3310(9) . ? N3 C11 1.4736(10) . ? N3 C13 1.4766(10) . ? C1 C4 1.4056(9) . ? C1 C3 1.4259(11) . ? C1 C2 1.4258(11) . ? C4 C5 1.4968(9) . ? C5 C10 1.3963(10) . ? C5 C6 1.3963(10) . ? C6 C7 1.3945(11) . ? C6 H6A 0.90(2) . ? C7 C8 1.3925(13) . ? C7 H7A 0.85(2) . ? C8 C9 1.3949(14) . ? C8 H8A 0.93(2) . ? C9 C10 1.3985(12) . ? C9 H9A 0.88(3) . ? C10 H10A 0.89(2) . ? C11 C12 1.5227(13) . ? C11 H11A 0.95(2) . ? C11 H11B 0.94(2) . ? C12 H12A 0.94(3) . ? C12 H12B 0.95(3) . ? C12 H12C 0.94(3) . ? C13 C14 1.5207(14) . ? C13 H13A 0.92(2) . ? C13 H13B 0.94(2) . ? C14 H14A 0.91(4) . ? C14 H14B 1.03(3) . ? C14 H14C 0.98(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C4 N3 C11 122.65(6) . . ? C4 N3 C13 122.37(6) . . ? C11 N3 C13 114.95(6) . . ? C4 C1 C3 128.06(7) . . ? C4 C1 C2 118.44(7) . . ? C3 C1 C2 113.47(7) . . ? N1 C2 C1 176.92(9) . . ? N2 C3 C1 175.57(10) . . ? N3 C4 C1 126.90(6) . . ? N3 C4 C5 118.14(6) . . ? C1 C4 C5 114.96(6) . . ? C10 C5 C6 120.38(7) . . ? C10 C5 C4 119.32(6) . . ? C6 C5 C4 120.22(6) . . ? C7 C6 C5 119.77(7) . . ? C7 C6 H6A 121.4(15) . . ? C5 C6 H6A 118.9(15) . . ? C8 C7 C6 120.14(8) . . ? C8 C7 H7A 119.6(15) . . ? C6 C7 H7A 120.3(15) . . ? C7 C8 C9 120.03(7) . . ? C7 C8 H8A 119.6(15) . . ? C9 C8 H8A 120.3(15) . . ? C8 C9 C10 120.18(8) . . ? C8 C9 H9A 120.3(17) . . ? C10 C9 H9A 119.5(17) . . ? C5 C10 C9 119.48(7) . . ? C5 C10 H10A 119.6(13) . . ? C9 C10 H10A 120.8(13) . . ? N3 C11 C12 112.02(6) . . ? N3 C11 H11A 110.1(12) . . ? C12 C11 H11A 110.9(12) . . ? N3 C11 H11B 106.0(14) . . ? C12 C11 H11B 107.5(15) . . ? H11A C11 H11B 110.1(18) . . ? C11 C12 H12A 110.0(17) . . ? C11 C12 H12B 105.0(17) . . ? H12A C12 H12B 109.4(23) . . ? C11 C12 H12C 110.2(18) . . ? H12A C12 H12C 106.8(24) . . ? H12B C12 H12C 115.4(23) . . ? N3 C13 C14 112.31(7) . . ? N3 C13 H13A 108.6(13) . . ? C14 C13 H13A 111.4(13) . . ? N3 C13 H13B 106.3(13) . . ? C14 C13 H13B 108.6(13) . . ? H13A C13 H13B 109.4(18) . . ? C13 C14 H14A 107.6(23) . . ? C13 C14 H14B 107.7(19) . . ? H14A C14 H14B 108.7(30) . . ? C13 C14 H14C 114.1(19) . . ? H14A C14 H14C 112.3(30) . . ? H14B C14 H14C 106.3(26) . . ? 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 C1 C2 N1 170.4(16) . . . . ? C3 C1 C2 N1 -11.3(17) . . . . ? C4 C1 C3 N2 155.2(15) . . . . ? C2 C1 C3 N2 -22.9(15) . . . . ? C11 N3 C4 C1 3.92(11) . . . . ? C13 N3 C4 C1 -178.05(7) . . . . ? C11 N3 C4 C5 -175.94(6) . . . . ? C13 N3 C4 C5 2.09(10) . . . . ? C3 C1 C4 N3 9.88(13) . . . . ? C2 C1 C4 N3 -172.14(7) . . . . ? C3 C1 C4 C5 -170.25(8) . . . . ? C2 C1 C4 C5 7.73(10) . . . . ? N3 C4 C5 C10 -94.04(8) . . . . ? C1 C4 C5 C10 86.09(8) . . . . ? N3 C4 C5 C6 89.13(8) . . . . ? C1 C4 C5 C6 -90.75(8) . . . . ? C10 C5 C6 C7 -0.60(11) . . . . ? C4 C5 C6 C7 176.21(7) . . . . ? C5 C6 C7 C8 -0.41(13) . . . . ? C6 C7 C8 C9 1.07(13) . . . . ? C7 C8 C9 C10 -0.72(14) . . . . ? C6 C5 C10 C9 0.94(12) . . . . ? C4 C5 C10 C9 -175.90(7) . . . . ? C8 C9 C10 C5 -0.28(13) . . . . ? C4 N3 C11 C12 77.26(10) . . . . ? C13 N3 C11 C12 -100.90(8) . . . . ? C4 N3 C13 C14 103.86(10) . . . . ? C11 N3 C13 C14 -77.97(10) . . . . ? _refine_diff_density_max 0.224 _refine_diff_density_min -0.201 _refine_diff_density_rms 0.028 #==END data_4c _database_code_CSD 168511 _journal_coden_Cambridge 188 _publ_requested_journal 'Perkin Transactions 2' loop_ _publ_author_name 'Karlsen, Hege' 'Kolsaker, Per' 'Romming, Christian' 'Uggerud, Einar' _publ_contact_author_name 'Prof Per Kolsaker' _publ_contact_author_address ; Prof Per Kolsaker Department of Chemistry University of Oslo P OBox 1033 Blindern N-0315 Oslo NORWAY ; _publ_contact_author_email 'PER.KOLSAKER@KJEMI.UIO.NO' _publ_section_title ; The Analogy between C = O and C(CN)2. Part 2: Structural Properties of N,N-Dialkylbenzamides and the Analogously Substituted 2-(Phenylmethylene)propanedinitriles ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-(phenylpyrrolidin-1-yl-methylene)propanedinitrile ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H13 N3' _chemical_formula_weight 223.27 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' _symmetry_cell_setting ? _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.4580(7) _cell_length_b 14.1989(12) _cell_length_c 10.5332(9) _cell_angle_alpha 90.00 _cell_angle_beta 109.561(4) _cell_angle_gamma 90.00 _cell_volume 1191.97(17) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.8 _exptl_crystal_size_mid 0.5 _exptl_crystal_size_min 0.5 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.244 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 472 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 27729 _diffrn_reflns_av_R_equivalents 0.0246 _diffrn_reflns_av_sigmaI/netI 0.0178 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.50 _diffrn_reflns_theta_max 40.21 _reflns_number_total 7112 _reflns_number_gt 5450 _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^)+(0.0887P)^2^+0.1479P] 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_number_reflns 7112 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0729 _refine_ls_R_factor_gt 0.0540 _refine_ls_wR_factor_ref 0.1660 _refine_ls_wR_factor_gt 0.1470 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _refine_ls_shift/su_max 0.024 _refine_ls_shift/su_mean 0.002 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 -0.06452(10) 0.29124(6) 0.58354(8) 0.03643(16) Uani 1 1 d . . . N2 N -0.28828(9) 0.04175(6) 0.36911(10) 0.03926(17) Uani 1 1 d . . . C1 C -0.03176(8) 0.15290(4) 0.43477(6) 0.02141(11) Uani 1 1 d . A . C2 C -0.04703(9) 0.22996(5) 0.51668(7) 0.02529(12) Uani 1 1 d . . . C3 C -0.17189(8) 0.09074(5) 0.39579(8) 0.02644(13) Uani 1 1 d . . . C4 C 0.11560(7) 0.14315(4) 0.40266(6) 0.02046(10) Uani 1 1 d . . . C5 C 0.25013(8) 0.21561(4) 0.45588(7) 0.02248(11) Uani 1 1 d . A . C6 C 0.24686(10) 0.29731(5) 0.38152(8) 0.02937(14) Uani 1 1 d . . . H6 H 0.1534(18) 0.3078(10) 0.2953(14) 0.041(3) Uiso 1 1 d . . . C7 C 0.37619(12) 0.36308(6) 0.42709(10) 0.03549(17) Uani 1 1 d . A . H7 H 0.3772(18) 0.4212(10) 0.3733(14) 0.043(3) Uiso 1 1 d . . . C8 C 0.50781(11) 0.34716(6) 0.54592(11) 0.03696(18) Uani 1 1 d . . . H8 H 0.5990(19) 0.3920(11) 0.5778(15) 0.047(4) Uiso 1 1 d . . . C9 C 0.50991(11) 0.26620(7) 0.62069(11) 0.03981(19) Uani 1 1 d . A . H9 H 0.605(2) 0.2534(11) 0.7056(17) 0.058(4) Uiso 1 1 d . . . C10 C 0.38135(10) 0.19996(6) 0.57602(9) 0.03327(16) Uani 1 1 d . . . H10 H 0.3843(17) 0.1442(10) 0.6327(15) 0.043(3) Uiso 1 1 d . . . N3A N 0.1478(4) 0.0766(2) 0.3292(3) 0.0265(6) Uani 0.75 1 d P A 1 C11A C 0.0385(2) -0.00520(12) 0.26881(18) 0.0286(3) Uani 0.75 1 d P A 1 H11A H -0.0586 0.0147 0.1905 0.034 Uiso 0.75 1 calc PR A 1 H11B H -0.0033 -0.0357 0.3359 0.034 Uiso 0.75 1 calc PR A 1 C12A C 0.1526(2) -0.07180(10) 0.22509(19) 0.0499(4) Uani 0.75 1 d P A 1 H12A H 0.2135 -0.1149 0.2992 0.060 Uiso 0.75 1 calc PR A 1 H12B H 0.0874 -0.1096 0.1458 0.060 Uiso 0.75 1 calc PR A 1 C13A C 0.2731(5) -0.0057(2) 0.1900(3) 0.0427(6) Uani 0.75 1 d P A 1 H13A H 0.3791 -0.0382 0.1963 0.051 Uiso 0.75 1 calc PR A 1 H13B H 0.2223 0.0204 0.0981 0.051 Uiso 0.75 1 calc PR A 1 C14A C 0.3025(8) 0.0704(4) 0.2955(6) 0.0390(10) Uani 0.75 1 d P A 1 H14A H 0.321(3) 0.1293(15) 0.254(2) 0.044(5) Uiso 0.75 1 d P B 1 H14B H 0.403(3) 0.0608(17) 0.381(2) 0.049(6) Uiso 0.75 1 d P C 1 N3B N 0.1457(10) 0.0722(6) 0.3275(7) 0.0195(15) Uani 0.25 1 d P A 2 C11B C 0.0130(7) 0.0141(4) 0.2372(5) 0.0260(7) Uani 0.25 1 d P A 2 H11C H -0.0885 0.0518 0.1909 0.031 Uiso 0.25 1 calc PR A 2 H11D H -0.0176 -0.0386 0.2861 0.031 Uiso 0.25 1 calc PR A 2 C12B C 0.0963(5) -0.0211(3) 0.1393(4) 0.0399(8) Uani 0.25 1 d P A 2 H12C H 0.0559 -0.0848 0.1056 0.048 Uiso 0.25 1 calc PR A 2 H12D H 0.0753 0.0223 0.0617 0.048 Uiso 0.25 1 calc PR A 2 C13B C 0.2789(12) -0.0226(7) 0.2235(9) 0.0416(15) Uani 0.25 1 d P A 2 H13C H 0.3036 -0.0794 0.2813 0.050 Uiso 0.25 1 calc PR A 2 H13D H 0.3485 -0.0249 0.1644 0.050 Uiso 0.25 1 calc PR A 2 C14B C 0.320(2) 0.0639(14) 0.3092(15) 0.032(2) Uani 0.25 1 d P A 2 H14C H 0.376(6) 0.124(4) 0.315(5) 0.023(10) Uiso 0.25 1 d P D 2 H14D H 0.381(6) 0.021(3) 0.391(5) 0.021(10) Uiso 0.25 1 d P E 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 N1 0.0355(3) 0.0382(4) 0.0384(3) -0.0074(3) 0.0161(3) 0.0013(3) N2 0.0247(3) 0.0368(3) 0.0581(5) -0.0048(3) 0.0162(3) -0.0075(2) C1 0.0180(2) 0.0222(2) 0.0246(2) 0.00108(18) 0.00786(18) -0.00131(17) C2 0.0224(3) 0.0278(3) 0.0264(3) 0.0011(2) 0.0093(2) 0.0008(2) C3 0.0199(2) 0.0264(3) 0.0334(3) 0.0021(2) 0.0093(2) -0.00067(19) C4 0.0181(2) 0.0200(2) 0.0232(2) 0.00123(17) 0.00691(18) -0.00070(16) C5 0.0186(2) 0.0212(2) 0.0285(3) -0.00194(19) 0.0089(2) -0.00183(17) C6 0.0301(3) 0.0238(3) 0.0336(3) 0.0005(2) 0.0098(3) -0.0056(2) C7 0.0382(4) 0.0265(3) 0.0448(4) -0.0033(3) 0.0178(3) -0.0109(3) C8 0.0279(3) 0.0316(3) 0.0518(5) -0.0124(3) 0.0139(3) -0.0099(3) C9 0.0269(3) 0.0344(4) 0.0479(5) -0.0067(3) -0.0010(3) -0.0046(3) C10 0.0277(3) 0.0283(3) 0.0364(4) 0.0006(3) 0.0010(3) -0.0037(2) N3A 0.0202(9) 0.0254(10) 0.0341(11) -0.0037(7) 0.0092(7) -0.0066(7) C11A 0.0303(7) 0.0266(7) 0.0313(8) -0.0063(4) 0.0136(6) -0.0078(5) C12A 0.0625(9) 0.0321(5) 0.0734(10) -0.0212(6) 0.0470(8) -0.0131(5) C13A 0.0475(11) 0.0427(12) 0.0510(13) -0.0156(8) 0.0337(11) -0.0105(9) C14A 0.0249(13) 0.0363(11) 0.063(3) -0.0187(15) 0.0241(16) -0.0060(11) N3B 0.028(3) 0.0166(19) 0.021(2) -0.0039(14) 0.018(2) 0.0055(17) C11B 0.0250(16) 0.0256(19) 0.0262(19) -0.0063(12) 0.0070(14) -0.0035(12) C12B 0.0346(15) 0.0459(19) 0.0400(16) -0.0206(15) 0.0134(13) -0.0030(13) C13B 0.032(2) 0.038(3) 0.058(5) -0.017(3) 0.020(3) 0.006(2) C14B 0.023(3) 0.045(4) 0.0309(19) -0.0066(19) 0.0113(18) 0.003(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 C2 1.1596(10) . ? N2 C3 1.1604(10) . ? C1 C4 1.4034(9) . ? C1 C3 1.4236(9) . ? C1 C2 1.4258(9) . ? C4 N3A 1.306(3) . ? C4 N3B 1.357(6) . ? C4 C5 1.4968(8) . ? C5 C10 1.3935(10) . ? C5 C6 1.3948(10) . ? C6 C7 1.3956(11) . ? C6 H6 0.995(14) . ? C7 C8 1.3870(14) . ? C7 H7 1.003(14) . ? C8 C9 1.3901(14) . ? C8 H8 0.969(15) . ? C9 C10 1.3949(11) . ? C9 H9 0.998(17) . ? C10 H10 0.987(14) . ? N3A C14A 1.468(7) . ? N3A C11A 1.489(4) . ? C11A C12A 1.528(2) . ? C11A H11A 0.9900 . ? C11A H11B 0.9900 . ? C12A C13A 1.519(3) . ? C12A H12A 0.9900 . ? C12A H12B 0.9900 . ? C13A C14A 1.510(7) . ? C13A H13A 0.9900 . ? C13A H13B 0.9900 . ? C14A H14A 0.98(2) . ? C14A H14B 1.02(2) . ? C14A H14C 0.96(5) . ? C14A H14D 1.23(5) . ? N3B C11B 1.460(10) . ? N3B C14B 1.55(2) . ? C11B C12B 1.516(7) . ? C11B H11C 0.9900 . ? C11B H11D 0.9900 . ? C12B C13B 1.502(11) . ? C12B H12C 0.9900 . ? C12B H12D 0.9900 . ? C13B C14B 1.50(2) . ? C13B H13C 0.9900 . ? C13B H13D 0.9900 . ? C14B H14A 1.10(3) . ? C14B H14B 0.84(3) . ? C14B H14C 0.97(5) . ? C14B H14D 1.04(5) . ? 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 C4 C1 C3 126.17(6) . . ? C4 C1 C2 119.29(6) . . ? C3 C1 C2 114.52(6) . . ? N1 C2 C1 177.62(8) . . ? N2 C3 C1 176.71(9) . . ? N3A C4 N3B 1.8(5) . . ? N3A C4 C1 126.34(14) . . ? N3B C4 C1 124.7(3) . . ? N3A C4 C5 115.82(13) . . ? N3B C4 C5 117.5(3) . . ? C1 C4 C5 117.84(5) . . ? C10 C5 C6 120.17(6) . . ? C10 C5 C4 120.33(6) . . ? C6 C5 C4 119.45(6) . . ? C5 C6 C7 119.84(7) . . ? C5 C6 H6 119.8(8) . . ? C7 C6 H6 120.3(8) . . ? C8 C7 C6 120.07(8) . . ? C8 C7 H7 119.2(8) . . ? C6 C7 H7 120.7(8) . . ? C7 C8 C9 120.01(7) . . ? C7 C8 H8 120.7(9) . . ? C9 C8 H8 119.3(9) . . ? C8 C9 C10 120.39(8) . . ? C8 C9 H9 120.8(9) . . ? C10 C9 H9 118.8(9) . . ? C5 C10 C9 119.51(8) . . ? C5 C10 H10 121.9(8) . . ? C9 C10 H10 118.6(8) . . ? C4 N3A C14A 124.5(3) . . ? C4 N3A C11A 126.4(2) . . ? C14A N3A C11A 109.0(3) . . ? N3A C11A C12A 104.30(17) . . ? N3A C11A H11A 110.9 . . ? C12A C11A H11A 110.9 . . ? N3A C11A H11B 110.9 . . ? C12A C11A H11B 110.9 . . ? H11A C11A H11B 108.9 . . ? C13A C12A C11A 103.53(17) . . ? C13A C12A H12A 111.1 . . ? C11A C12A H12A 111.1 . . ? C13A C12A H12B 111.1 . . ? C11A C12A H12B 111.1 . . ? H12A C12A H12B 109.0 . . ? C14A C13A C12A 102.8(3) . . ? C14A C13A H13A 111.2 . . ? C12A C13A H13A 111.2 . . ? C14A C13A H13B 111.2 . . ? C12A C13A H13B 111.2 . . ? H13A C13A H13B 109.1 . . ? N3A C14A C13A 106.3(4) . . ? N3A C14A H14A 110.2(13) . . ? C13A C14A H14A 106.9(13) . . ? N3A C14A H14B 110.0(14) . . ? C13A C14A H14B 115.9(15) . . ? H14A C14A H14B 107.5(18) . . ? N3A C14A H14C 118(3) . . ? C13A C14A H14C 131(3) . . ? H14A C14A H14C 40(3) . . ? H14B C14A H14C 69(3) . . ? N3A C14A H14D 97(2) . . ? C13A C14A H14D 96(2) . . ? H14A C14A H14D 137(3) . . ? H14B C14A H14D 30(2) . . ? H14C C14A H14D 98(4) . . ? C4 N3B C11B 123.1(6) . . ? C4 N3B C14B 120.0(9) . . ? C11B N3B C14B 115.5(8) . . ? N3B C11B C12B 101.4(4) . . ? N3B C11B H11C 111.5 . . ? C12B C11B H11C 111.5 . . ? N3B C11B H11D 111.5 . . ? C12B C11B H11D 111.5 . . ? H11C C11B H11D 109.3 . . ? C13B C12B C11B 102.9(4) . . ? C13B C12B H12C 111.2 . . ? C11B C12B H12C 111.2 . . ? C13B C12B H12D 111.2 . . ? C11B C12B H12D 111.2 . . ? H12C C12B H12D 109.1 . . ? C14B C13B C12B 109.2(9) . . ? C14B C13B H13C 109.8 . . ? C12B C13B H13C 109.8 . . ? C14B C13B H13D 109.8 . . ? C12B C13B H13D 109.8 . . ? H13C C13B H13D 108.3 . . ? C13B C14B N3B 95.7(11) . . ? C13B C14B H14A 114.5(17) . . ? N3B C14B H14A 100.3(18) . . ? C13B C14B H14B 117(2) . . ? N3B C14B H14B 116(2) . . ? H14A C14B H14B 112(3) . . ? C13B C14B H14C 140(3) . . ? N3B C14B H14C 113(3) . . ? H14A C14B H14C 36(3) . . ? H14B C14B H14C 76(3) . . ? C13B C14B H14D 88(3) . . ? N3B C14B H14D 100(3) . . ? H14A C14B H14D 148(3) . . ? H14B C14B H14D 36(3) . . ? H14C C14B H14D 112(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 C4 C1 C2 N1 -171.4(19) . . . . ? C3 C1 C2 N1 7.1(19) . . . . ? C4 C1 C3 N2 158.7(14) . . . . ? C2 C1 C3 N2 -19.8(15) . . . . ? C3 C1 C4 N3A 1.6(2) . . . . ? C2 C1 C4 N3A 180.0(2) . . . . ? C3 C1 C4 N3B 0.6(4) . . . . ? C2 C1 C4 N3B 179.0(4) . . . . ? C3 C1 C4 C5 -178.86(6) . . . . ? C2 C1 C4 C5 -0.51(9) . . . . ? N3A C4 C5 C10 -85.74(19) . . . . ? N3B C4 C5 C10 -84.8(4) . . . . ? C1 C4 C5 C10 94.71(8) . . . . ? N3A C4 C5 C6 91.69(19) . . . . ? N3B C4 C5 C6 92.6(4) . . . . ? C1 C4 C5 C6 -87.87(8) . . . . ? C10 C5 C6 C7 0.56(12) . . . . ? C4 C5 C6 C7 -176.86(7) . . . . ? C5 C6 C7 C8 0.12(13) . . . . ? C6 C7 C8 C9 -0.84(14) . . . . ? C7 C8 C9 C10 0.90(15) . . . . ? C6 C5 C10 C9 -0.51(13) . . . . ? C4 C5 C10 C9 176.89(8) . . . . ? C8 C9 C10 C5 -0.21(15) . . . . ? N3B C4 N3A C14A -155(17) . . . . ? C1 C4 N3A C14A 178.5(3) . . . . ? C5 C4 N3A C14A -1.0(5) . . . . ? N3B C4 N3A C11A 24(16) . . . . ? C1 C4 N3A C11A -2.9(4) . . . . ? C5 C4 N3A C11A 177.6(2) . . . . ? C4 N3A C11A C12A -166.3(3) . . . . ? C14A N3A C11A C12A 12.5(4) . . . . ? N3A C11A C12A C13A -31.0(2) . . . . ? C11A C12A C13A C14A 37.5(4) . . . . ? C4 N3A C14A C13A -170.0(3) . . . . ? C11A N3A C14A C13A 11.2(5) . . . . ? C12A C13A C14A N3A -30.3(5) . . . . ? N3A C4 N3B C11B -134(17) . . . . ? C1 C4 N3B C11B 19.4(9) . . . . ? C5 C4 N3B C11B -161.1(5) . . . . ? N3A C4 N3B C14B 32(16) . . . . ? C1 C4 N3B C14B -174.6(8) . . . . ? C5 C4 N3B C14B 4.9(11) . . . . ? C4 N3B C11B C12B 156.7(6) . . . . ? C14B N3B C11B C12B -9.8(10) . . . . ? N3B C11B C12B C13B 29.1(6) . . . . ? C11B C12B C13B C14B -41.6(9) . . . . ? C12B C13B C14B N3B 32.6(10) . . . . ? C4 N3B C14B C13B 179.5(7) . . . . ? C11B N3B C14B C13B -13.5(12) . . . . ? _diffrn_measured_fraction_theta_max 0.951 _diffrn_reflns_theta_full 40.21 _diffrn_measured_fraction_theta_full 0.951 _refine_diff_density_max 0.446 _refine_diff_density_min -0.263 _refine_diff_density_rms 0.060 data_5a _database_code_CSD 168512 _audit_creation_method SHELXL-97 _chemical_name_systematic ; N,N-dimetyl-benzamide ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H11 N O' _chemical_formula_weight 149.19 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 'P2(1)2(1)2(1)' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 6.6312(5) _cell_length_b 7.6519(6) _cell_length_c 16.3025(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 827.21(11) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.8 _exptl_crystal_size_mid 0.6 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.198 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 320 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type SADABS _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 16518 _diffrn_reflns_av_R_equivalents 0.0301 _diffrn_reflns_av_sigmaI/netI 0.0214 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 8.23 _diffrn_reflns_theta_max 40.01 _reflns_number_total 4831 _reflns_number_gt 4433 _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^)+(0.0630P)^2^+0.0400P] 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 0.7(8) _refine_ls_number_reflns 4831 _refine_ls_number_parameters 144 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0462 _refine_ls_R_factor_gt 0.0399 _refine_ls_wR_factor_ref 0.1092 _refine_ls_wR_factor_gt 0.1030 _refine_ls_goodness_of_fit_ref 1.138 _refine_ls_restrained_S_all 1.138 _refine_ls_shift/su_max 0.012 _refine_ls_shift/su_mean 0.002 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 1.21437(9) 0.15748(9) 0.19790(4) 0.02870(12) Uani 1 1 d . . . N1 N 0.87964(9) 0.09714(8) 0.19412(4) 0.02167(10) Uani 1 1 d . . . C4 C 1.06446(9) 0.10522(8) 0.15942(4) 0.01865(9) Uani 1 1 d . . . C5 C 1.08769(8) 0.05291(8) 0.07098(3) 0.01691(9) Uani 1 1 d . . . C6 C 0.96819(10) 0.12545(9) 0.00893(4) 0.02128(11) Uani 1 1 d . . . H6 H 0.860(2) 0.2071(18) 0.0217(9) 0.030(3) Uiso 1 1 d . . . C7 C 1.00550(12) 0.08411(10) -0.07323(4) 0.02473(12) Uani 1 1 d . . . H7 H 0.918(2) 0.139(2) -0.1152(10) 0.038(4) Uiso 1 1 d . . . C8 C 1.16106(13) -0.02991(10) -0.09391(4) 0.02643(13) Uani 1 1 d . . . H8 H 1.189(2) -0.057(2) -0.1485(10) 0.035(4) Uiso 1 1 d . . . C9 C 1.28085(11) -0.10212(10) -0.03215(4) 0.02446(12) Uani 1 1 d . . . H9 H 1.398(3) -0.182(3) -0.0432(11) 0.049(4) Uiso 1 1 d . . . C10 C 1.24557(9) -0.05994(9) 0.04984(4) 0.01975(10) Uani 1 1 d . . . H10 H 1.335(2) -0.112(2) 0.0931(9) 0.033(3) Uiso 1 1 d . . . C11 C 0.85541(15) 0.15927(14) 0.27798(5) 0.03453(18) Uani 1 1 d . . . H11A H 0.852(3) 0.064(3) 0.3134(13) 0.056(5) Uiso 1 1 d . . . H11B H 0.715(4) 0.211(3) 0.2836(16) 0.069(6) Uiso 1 1 d . . . H11C H 0.971(3) 0.239(3) 0.2895(12) 0.053(5) Uiso 1 1 d . . . C12 C 0.70667(11) 0.00246(10) 0.16159(5) 0.02501(12) Uani 1 1 d . . . H12A H 0.677(3) -0.098(2) 0.2002(11) 0.042(4) Uiso 1 1 d . . . H12B H 0.733(3) -0.038(2) 0.1100(11) 0.037(4) Uiso 1 1 d . . . H12C H 0.586(3) 0.075(2) 0.1600(10) 0.039(4) 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 0.0204(2) 0.0439(3) 0.0219(2) -0.0062(2) -0.00086(16) -0.0087(2) N1 0.0178(2) 0.0249(2) 0.0223(2) -0.00486(18) 0.00419(16) -0.00280(16) C4 0.0173(2) 0.0206(2) 0.0180(2) -0.00161(17) 0.00081(16) -0.00182(17) C5 0.0151(2) 0.0181(2) 0.01758(19) -0.00113(16) -0.00054(15) -0.00037(16) C6 0.0202(2) 0.0221(2) 0.0215(2) 0.00015(18) -0.00268(17) 0.00289(19) C7 0.0271(3) 0.0273(3) 0.0198(2) 0.0007(2) -0.0053(2) -0.0004(2) C8 0.0308(3) 0.0287(3) 0.0197(2) -0.0048(2) 0.0001(2) -0.0009(2) C9 0.0241(3) 0.0251(3) 0.0241(2) -0.0049(2) 0.0028(2) 0.0035(2) C10 0.0171(2) 0.0208(2) 0.0213(2) -0.00025(18) -0.00003(16) 0.00163(17) C11 0.0324(4) 0.0451(5) 0.0261(3) -0.0120(3) 0.0105(3) -0.0087(3) C12 0.0165(2) 0.0272(3) 0.0313(3) -0.0020(2) 0.0010(2) -0.0030(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 O1 C4 1.2416(8) . ? N1 C4 1.3512(8) . ? N1 C11 1.4564(10) . ? N1 C12 1.4565(9) . ? C4 C5 1.5044(8) . ? C5 C6 1.3997(9) . ? C5 C10 1.4001(9) . ? C6 C7 1.3983(10) . ? C6 H6 0.973(14) . ? C7 C8 1.3925(11) . ? C7 H7 0.992(16) . ? C8 C9 1.3964(11) . ? C8 H8 0.932(17) . ? C9 C10 1.3949(9) . ? C9 H9 1.00(2) . ? C10 H10 1.005(15) . ? C11 H11A 0.93(2) . ? C11 H11B 1.01(2) . ? C11 H11C 1.00(2) . ? C12 H12A 1.016(17) . ? C12 H12B 0.913(17) . ? C12 H12C 0.974(17) . ? 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 C4 N1 C11 118.56(6) . . ? C4 N1 C12 125.78(6) . . ? C11 N1 C12 114.66(6) . . ? O1 C4 N1 121.97(6) . . ? O1 C4 C5 119.21(5) . . ? N1 C4 C5 118.81(5) . . ? C6 C5 C10 119.35(5) . . ? C6 C5 C4 121.95(5) . . ? C10 C5 C4 118.46(5) . . ? C7 C6 C5 120.15(6) . . ? C7 C6 H6 118.7(8) . . ? C5 C6 H6 121.2(8) . . ? C8 C7 C6 120.31(6) . . ? C8 C7 H7 122.2(9) . . ? C6 C7 H7 117.5(9) . . ? C7 C8 C9 119.65(6) . . ? C7 C8 H8 121.2(10) . . ? C9 C8 H8 119.1(10) . . ? C10 C9 C8 120.26(6) . . ? C10 C9 H9 116.3(10) . . ? C8 C9 H9 123.4(10) . . ? C9 C10 C5 120.26(6) . . ? C9 C10 H10 118.8(9) . . ? C5 C10 H10 120.9(9) . . ? N1 C11 H11A 109.1(13) . . ? N1 C11 H11B 108.3(14) . . ? H11A C11 H11B 103(2) . . ? N1 C11 H11C 106.9(12) . . ? H11A C11 H11C 112.4(17) . . ? H11B C11 H11C 116.5(17) . . ? N1 C12 H12A 107.7(10) . . ? N1 C12 H12B 110.7(11) . . ? H12A C12 H12B 110.5(15) . . ? N1 C12 H12C 112.0(10) . . ? H12A C12 H12C 106.8(15) . . ? H12B C12 H12C 109.0(15) . . ? 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 C11 N1 C4 O1 2.81(11) . . . . ? C12 N1 C4 O1 -165.08(7) . . . . ? C11 N1 C4 C5 -175.83(7) . . . . ? C12 N1 C4 C5 16.28(10) . . . . ? O1 C4 C5 C6 -125.73(8) . . . . ? N1 C4 C5 C6 52.96(9) . . . . ? O1 C4 C5 C10 48.52(9) . . . . ? N1 C4 C5 C10 -132.79(7) . . . . ? C10 C5 C6 C7 0.55(10) . . . . ? C4 C5 C6 C7 174.75(6) . . . . ? C5 C6 C7 C8 0.26(11) . . . . ? C6 C7 C8 C9 -0.42(12) . . . . ? C7 C8 C9 C10 -0.23(12) . . . . ? C8 C9 C10 C5 1.04(11) . . . . ? C6 C5 C10 C9 -1.20(9) . . . . ? C4 C5 C10 C9 -175.60(6) . . . . ? _diffrn_measured_fraction_theta_max 0.952 _diffrn_reflns_theta_full 40.01 _diffrn_measured_fraction_theta_full 0.952 _refine_diff_density_max 0.493 _refine_diff_density_min -0.271 _refine_diff_density_rms 0.052