# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 #TrackingRef 'NxxM_5-Cl-NoxM_fin.cif' #============================================================ _audit_creation_date 'July 11, 2010' _audit_creation_method 'from Oxford Diffraction CIF routine and SHELXL97' _audit_update_record ; July 11, 2010 Assembled, pass-1 July 14, 2010 Text and experimental details added January 22, 2010 Final preparation of 9 molecule CIF. ; #============================================================ # 1. SUBMISSION DETAILS _publ_contact_author_name 'Dr. John F. Gallagher' _publ_contact_author_address ; School of Chemical Sciences, Dublin City University, Dublin 9, Ireland ; _publ_contact_author_phone '353 1 7005114' _publ_contact_author_fax '353 1 7005503' _publ_contact_author_email john.gallagher@dcu.ie _publ_requested_category ? _publ_requested_coeditor_name 'The RSC Technical Editor or The CSD archive' _publ_contact_letter ; January 24th, 2011 Please consider this CIF submission for deposition on the CSD. The authors have seen and approved of this submission. It is intended that this work will be submitted shortly to the RSC Journal Cryst. Eng. Commun. in January 2011. The CIF has passed the Chester CHECKCIF routines and gives a satisfactory PRINTCIF file. All structures solved and refined without problems although some structures exhibited CH3 rotational disorder and were treated using AFIX 127. We request CSD codes for these twelve crystal structures of a 3 x 3 isomer grid and 3 chlorinated analogues and NmpFM a structure which contains a 1:1 ration of NmpF and NmpM. The 3 x 3 NxxM isomer grid compounds are the isomers of the Mxx series published by us in 2010 as follows: P. Mocilac, M. Tallon, A.J. Lough, J.F. Gallagher CrystEngComm, 2010, 12, 3080--3090. I look forward to hearing from you soon. John Gallagher ; #============================================================ # 2. PROCESSING SUMMARY (IUCr Office Use Only) _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_date_printers_first ? _journal_date_printers_final ? _journal_date_proofs_out ? _journal_date_proofs_in ? _journal_coeditor_name ? _journal_coeditor_code ? _journal_coeditor_notes ; ? ; _journal_techeditor_code ? _journal_techeditor_notes ; ? ; _journal_coden_ASTM ? _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? #=========================================================== # 3. TITLE AND AUTHOR LIST _publ_section_title ; Synthesis, structural and DFT Studies of a 3x3 isomer grid of nine Methyl(benzene)nicotinamides and three Methyl(benzene)chloronicotinamides and a mixed NmpF:NmpM crystal structure as NmpFM. ; loop_ _publ_author_name _publ_author_address P.Mocilac ; School of Chemical Sciences, Dublin City University, Dublin 9, Ireland ; J.F.Gallagher ; School of Chemical Sciences, Dublin City University, Dublin 9, Ireland ; _publ_section_related_literature ; For background information, see: Gallagher et al., (2009a,b). ; #=========================================================== # 4. TEXT _publ_section_abstract ; The nine title compounds were synthesised from condensation reactions. The chlorinated derivatives were isolated and crystallised. ; _publ_section_comment ; >From the condensation reactions we crystallized nine isomeric nicotinamides and three chloronicotinamides. ; _publ_section_exptl_prep ; Compounds (I) to (IX), compounds (X) to (XII). ; _publ_section_exptl_refinement ; H atoms attached to C atoms were treated as riding using the SHELXL97 (Sheldrick, 2008) defaults at 150(1) K with C-H = 0.95 \%A (aromatic) and U~iso~(H) = 1.2U~eq~(C) (aromatic). The methyl C-H = 0.98 \%A (aliphatic) and U~iso~(H) = 1.5U~eq~(C). The N-H H atoms were refined with isotropic displacement parameters. ; _publ_section_references ; Allen, F.H. (2002). Acta Cryst. B58, 380--388. Chopra, D. & Row, T.N.G. (2008). CrystEngComm, 10, 54-67. Donnelly, K., Gallagher, J.F. & Lough, A.J. (2008). Acta Cryst. C64, o335-o340. Ferguson, G. (1998). PREP8. University of Guelph, Canada. Flack, H.D. (1983), Acta Cryst. A39, 876-881. Gallagher, J. F., McMahon, J., Anderson, F. P. & Lough, A. J. (2008). Acta Cryst. E64, o2394--o2394. Gelbrich, T., Hursthouse, M.B. & Threlfall, T.L. (2007). Acta Cryst. B63, 621--632. Nonius (1997). KappaCCD Server Software. Windows 3.11 Version. Nonius BV, Delft, The Netherlands. McArdle, P., (1995). J. Appl. Cryst. 28, 65--65. McMahon, J., Anderson, F.P., Gallagher, J.F. & Lough, A.J. (2008). Acta Cryst. C64, o493-o497. Oxford Diffraction (2010). CrysAlis CCD and Crysalis RED. Versions 1.172.33.55. Oxford Diffraction, Yarnton, Oxfordshire, U.K. Sheldrick, G.M. (2008). Acta Cryst. A64, 112--122. Spek, A. L. (2003). J. Appl. Cryst. 36, 7--13. ; _publ_section_figure_captions ; Fig. 1. A view of (I) to (IX) with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. ORTEP diagrams of the molecular structures of nine isomers from (I) to (IX). Fig. 2. A view of the C-H...X interactions in the crystal structure of (I) to (IX). ; _publ_section_table_legends ; Table 1. Hydrogen bond geometry (\%A, \%) for (I) to (IX). ; _publ_section_acknowledgements ; JFG thanks Dublin City University for grants in aid of chemical research. PM thanks the T3 (PRTLI-4) program for a studentship. ; #============================================================ data_NppM_[10-002] _database_code_depnum_ccdc_archive 'CCDC 809618' #TrackingRef 'NxxM_5-Cl-NoxM_fin.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common NppM _chemical_melting_point 435 _chemical_formula_moiety 'C13 H12 N2 O' _chemical_formula_sum 'C13 H12 N2 O' _chemical_formula_weight 212.25 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 Monoclinic _symmetry_space_group_name_H-M 'P 2/c' _symmetry_space_group_name_Hall '-P 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' '-x, -y, -z' '-x, y, -z-1/2' _cell_length_a 7.7391(4) _cell_length_b 5.2338(2) _cell_length_c 26.9102(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.321(5) _cell_angle_gamma 90.00 _cell_volume 1089.98(9) _cell_formula_units_Z 4 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 2594 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.53 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.293 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type Analytical _exptl_absorpt_correction_T_min 0.966 _exptl_absorpt_correction_T_max 0.988 _exptl_absorpt_process_details '(ABSFAC. Clark & Reid, 1998)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Xcalibur, Sapphire3, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_standards_number 8893 _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 1 _diffrn_reflns_number 8356 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0468 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_theta_min 3.89 _diffrn_reflns_theta_max 29.34 _diffrn_measured_fraction_theta_max 0.943 _diffrn_reflns_theta_full 29.34 _diffrn_measured_fraction_theta_full 0.970 _reflns_number_total 8356 _reflns_number_gt 5194 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008) and SORTX (McArdle, 1995)' _computing_molecular_graphics 'PLATON (Spek, 2009)' _computing_publication_material SHELXL97 _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 'w=1/[\s^2^(Fo^2^)+(0.0713P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0116(18) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 8356 _refine_ls_number_parameters 152 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0816 _refine_ls_R_factor_gt 0.0512 _refine_ls_wR_factor_ref 0.1405 _refine_ls_wR_factor_gt 0.1285 _refine_ls_goodness_of_fit_ref 0.970 _refine_ls_restrained_S_all 0.970 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.301 _refine_diff_density_min -0.247 _refine_diff_density_rms 0.052 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.75259(19) -0.12131(16) 0.48039(3) 0.0580(3) Uani 1 1 d . . . N1 N 0.74235(18) 0.3023(2) 0.46323(4) 0.0377(3) Uani 1 1 d . . . H1 H 0.7447(18) 0.446(2) 0.4766(4) 0.042(4) Uiso 1 1 d . . . C1 C 0.7494(2) 0.1012(2) 0.49417(5) 0.0386(3) Uani 1 1 d . . . C11 C 0.7416(2) 0.2908(2) 0.41026(4) 0.0340(3) Uani 1 1 d . . . C12 C 0.65647(19) 0.1002(3) 0.38487(5) 0.0401(3) Uani 1 1 d . . . H12 H 0.5979 -0.0269 0.4021 0.048 Uiso 1 1 calc R . . C13 C 0.6588(2) 0.0992(3) 0.33354(6) 0.0448(4) Uani 1 1 d . . . H13 H 0.6014 -0.0308 0.3167 0.054 Uiso 1 1 calc R . . C14 C 0.7439(2) 0.2856(3) 0.30625(5) 0.0435(3) Uani 1 1 d . . . C15 C 0.8273(2) 0.4772(3) 0.33273(5) 0.0453(4) Uani 1 1 d . . . H15 H 0.8846 0.6060 0.3156 0.054 Uiso 1 1 calc R . . C16 C 0.82668(19) 0.4799(2) 0.38398(5) 0.0411(3) Uani 1 1 d . . . H16 H 0.8838 0.6096 0.4010 0.049 Uiso 1 1 calc R . . C17 C 0.7472(3) 0.2803(3) 0.25049(5) 0.0687(5) Uani 1 1 d . . . H17A H 0.7916 0.1188 0.2395 0.103 Uiso 0.50 1 calc PR . . H17B H 0.8201 0.4153 0.2386 0.103 Uiso 0.50 1 calc PR . . H17C H 0.6322 0.3034 0.2378 0.103 Uiso 0.50 1 calc PR . . H17D H 0.7043 0.4395 0.2377 0.103 Uiso 0.50 1 calc PR . . H17E H 0.6758 0.1430 0.2386 0.103 Uiso 0.50 1 calc PR . . H17F H 0.8637 0.2549 0.2395 0.103 Uiso 0.50 1 calc PR . . C21 C 0.7542(2) 0.1621(2) 0.54864(4) 0.0330(3) Uani 1 1 d . . . C22 C 0.67288(19) 0.3692(2) 0.57036(5) 0.0407(3) Uani 1 1 d . . . H22 H 0.6159 0.4896 0.5508 0.049 Uiso 1 1 calc R . . C23 C 0.6777(2) 0.3945(3) 0.62164(5) 0.0465(4) Uani 1 1 d . . . H23 H 0.6205 0.5326 0.6358 0.056 Uiso 1 1 calc R . . N24 N 0.7593(2) 0.2329(2) 0.65176(4) 0.0472(3) Uani 1 1 d . . . C25 C 0.8380(2) 0.0378(3) 0.62995(5) 0.0479(4) Uani 1 1 d . . . H25 H 0.8970 -0.0768 0.6503 0.058 Uiso 1 1 calc R . . C26 C 0.83890(19) -0.0077(3) 0.57967(5) 0.0396(3) Uani 1 1 d . . . H26 H 0.8953 -0.1497 0.5668 0.048 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 O1 0.1060(9) 0.0302(5) 0.0378(6) -0.0032(4) -0.0017(8) 0.0022(6) N1 0.0592(7) 0.0266(5) 0.0274(6) -0.0015(4) 0.0015(7) 0.0003(6) C1 0.0483(7) 0.0317(6) 0.0359(7) -0.0002(5) 0.0018(8) -0.0005(7) C11 0.0445(7) 0.0293(5) 0.0282(6) 0.0005(5) 0.0005(8) 0.0059(6) C12 0.0478(8) 0.0377(7) 0.0346(8) 0.0031(6) 0.0001(7) -0.0075(6) C13 0.0513(8) 0.0450(8) 0.0381(9) -0.0058(6) -0.0072(8) -0.0057(7) C14 0.0475(7) 0.0522(8) 0.0309(7) 0.0004(6) -0.0013(9) 0.0059(8) C15 0.0558(9) 0.0435(8) 0.0366(8) 0.0058(6) 0.0049(8) -0.0045(7) C16 0.0523(8) 0.0341(7) 0.0368(8) -0.0023(6) -0.0002(7) -0.0060(7) C17 0.0751(10) 0.0992(12) 0.0317(8) -0.0031(8) -0.0004(11) -0.0113(11) C21 0.0403(6) 0.0312(6) 0.0274(6) 0.0008(5) 0.0028(8) -0.0049(6) C22 0.0495(8) 0.0358(7) 0.0368(8) 0.0015(6) -0.0007(7) 0.0007(6) C23 0.0601(9) 0.0397(8) 0.0399(9) -0.0060(6) 0.0055(8) -0.0015(7) N24 0.0616(7) 0.0475(6) 0.0325(6) -0.0016(5) 0.0030(7) -0.0050(7) C25 0.0620(10) 0.0441(8) 0.0377(9) 0.0055(6) -0.0043(8) -0.0007(7) C26 0.0464(8) 0.0352(7) 0.0372(8) 0.0015(6) 0.0013(7) 0.0012(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.2224(13) . ? N1 C1 1.3428(15) . ? N1 C11 1.4268(15) . ? N1 H1 0.832(13) . ? C1 C21 1.5005(16) . ? C11 C12 1.3755(18) . ? C11 C16 1.3846(18) . ? C12 C13 1.3815(18) . ? C12 H12 0.9300 . ? C13 C14 1.389(2) . ? C13 H13 0.9300 . ? C14 C15 1.387(2) . ? C14 C17 1.5011(17) . ? C15 C16 1.3792(17) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C17 H17D 0.9600 . ? C17 H17E 0.9600 . ? C17 H17F 0.9600 . ? C21 C26 1.3821(17) . ? C21 C22 1.3845(18) . ? C22 C23 1.3867(18) . ? C22 H22 0.9300 . ? C23 N24 1.3286(18) . ? C23 H23 0.9300 . ? N24 C25 1.3273(18) . ? C25 C26 1.3739(17) . ? C25 H25 0.9300 . ? C26 H26 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 C1 N1 C11 125.90(11) . . ? C1 N1 H1 116.0(9) . . ? C11 N1 H1 118.0(9) . . ? O1 C1 N1 124.02(12) . . ? O1 C1 C21 119.89(11) . . ? N1 C1 C21 116.09(11) . . ? C12 C11 C16 119.51(12) . . ? C12 C11 N1 121.73(12) . . ? C16 C11 N1 118.75(12) . . ? C11 C12 C13 119.35(13) . . ? C11 C12 H12 120.3 . . ? C13 C12 H12 120.3 . . ? C12 C13 C14 122.35(13) . . ? C12 C13 H13 118.8 . . ? C14 C13 H13 118.8 . . ? C15 C14 C13 117.15(12) . . ? C15 C14 C17 121.09(14) . . ? C13 C14 C17 121.75(14) . . ? C16 C15 C14 121.12(13) . . ? C16 C15 H15 119.4 . . ? C14 C15 H15 119.4 . . ? C15 C16 C11 120.51(13) . . ? C15 C16 H16 119.7 . . ? C11 C16 H16 119.7 . . ? C14 C17 H17A 109.5 . . ? C14 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C14 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C14 C17 H17D 109.5 . . ? H17A C17 H17D 141.1 . . ? H17B C17 H17D 56.3 . . ? H17C C17 H17D 56.3 . . ? C14 C17 H17E 109.5 . . ? H17A C17 H17E 56.3 . . ? H17B C17 H17E 141.1 . . ? H17C C17 H17E 56.3 . . ? H17D C17 H17E 109.5 . . ? C14 C17 H17F 109.5 . . ? H17A C17 H17F 56.3 . . ? H17B C17 H17F 56.3 . . ? H17C C17 H17F 141.1 . . ? H17D C17 H17F 109.5 . . ? H17E C17 H17F 109.5 . . ? C26 C21 C22 117.63(12) . . ? C26 C21 C1 117.55(12) . . ? C22 C21 C1 124.75(13) . . ? C21 C22 C23 119.02(13) . . ? C21 C22 H22 120.5 . . ? C23 C22 H22 120.5 . . ? N24 C23 C22 123.80(13) . . ? N24 C23 H23 118.1 . . ? C22 C23 H23 118.1 . . ? C25 N24 C23 115.95(12) . . ? N24 C25 C26 125.02(14) . . ? N24 C25 H25 117.5 . . ? C26 C25 H25 117.5 . . ? C25 C26 C21 118.57(13) . . ? C25 C26 H26 120.7 . . ? C21 C26 H26 120.7 . . ? 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 C1 O1 -1.6(3) . . . . ? C11 N1 C1 C21 178.14(15) . . . . ? C1 N1 C11 C12 36.9(2) . . . . ? C1 N1 C11 C16 -144.31(16) . . . . ? C16 C11 C12 C13 0.7(2) . . . . ? N1 C11 C12 C13 179.51(14) . . . . ? C11 C12 C13 C14 -0.3(2) . . . . ? C12 C13 C14 C15 -0.3(2) . . . . ? C12 C13 C14 C17 179.21(17) . . . . ? C13 C14 C15 C16 0.6(2) . . . . ? C17 C14 C15 C16 -178.92(16) . . . . ? C14 C15 C16 C11 -0.3(2) . . . . ? C12 C11 C16 C15 -0.4(2) . . . . ? N1 C11 C16 C15 -179.26(14) . . . . ? O1 C1 C21 C26 29.3(2) . . . . ? N1 C1 C21 C26 -150.43(14) . . . . ? O1 C1 C21 C22 -147.35(17) . . . . ? N1 C1 C21 C22 32.9(2) . . . . ? C26 C21 C22 C23 -1.0(2) . . . . ? C1 C21 C22 C23 175.69(14) . . . . ? C21 C22 C23 N24 1.3(2) . . . . ? C22 C23 N24 C25 -0.5(2) . . . . ? C23 N24 C25 C26 -0.7(2) . . . . ? N24 C25 C26 C21 0.9(2) . . . . ? C22 C21 C26 C25 -0.1(2) . . . . ? C1 C21 C26 C25 -176.97(14) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # # Hydrogen bonding scheme # ======== ======= ====== # # D H A D-H H...A D...A D-H...A symm publ # - - - --- ----- ----- ------- ---- ---- N1 H1 O1 0.832(13) 2.270(13) 3.0529(14) 157.0(11) 1_565 yes C12 H12 O1 0.93 2.47 2.9126(17) 109 . yes C12 H12 Cg1 0.93 2.89 3.5835(16) 133 3_656 yes # C12 H12 C21 0.93 3.12 3.905(2) 144 3_656 no # C12 H12 C22 0.93 2.86 3.744(2) 160 3_656 no # C12 H12 C23 0.93 2.94 3.663(2) 136 3_656 no # C12 H12 N24 0.93 3.30 3.785(2) 115 3_656 no # C12 H12 C25 0.93 3.48 3.912(2) 111 3_656 no # C12 H12 C26 0.93 3.42 3.985(2) 121 3_656 no # Cg1 is the C~5~N aromatic ring centroids located at site 3_656 # Complete details for the C-H...\p(arene) interaction at 1-X,-Y,1-Z # Two C-H...pi from C16-H16 [3766] and C23-H23 [3666] are 0.1\%A longer. #============================================================ data_NpmM_[10-003] _database_code_depnum_ccdc_archive 'CCDC 809619' #TrackingRef 'NxxM_5-Cl-NoxM_fin.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common NpmM _chemical_melting_point 415 _chemical_formula_moiety 'C13 H12 N2 O' _chemical_formula_sum 'C13 H12 N2 O' _chemical_formula_weight 212.25 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 Monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.2919(3) _cell_length_b 10.2600(3) _cell_length_c 13.5713(4) _cell_angle_alpha 90.00 _cell_angle_beta 100.919(3) _cell_angle_gamma 90.00 _cell_volume 1133.67(6) _cell_formula_units_Z 4 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 2208 _cell_measurement_theta_min 3.6 _cell_measurement_theta_max 25.0 _exptl_crystal_description Plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.244 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type Analytical _exptl_absorpt_correction_T_min 0.970 _exptl_absorpt_correction_T_max 0.995 _exptl_absorpt_process_details '(ABSFAC, Clark and Reid, 1998)' _exptl_special_details ; _reflns_odcompleteness_theta 23.21 ; _diffrn_ambient_temperature 294(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Xcalibur, Sapphire3, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_standards_number 2208 _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 1 _diffrn_reflns_number 5751 _diffrn_reflns_av_R_equivalents 0.0239 _diffrn_reflns_av_sigmaI/netI 0.0358 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.65 _diffrn_reflns_theta_max 25.09 _diffrn_measured_fraction_theta_max 0.912 _diffrn_reflns_theta_full 25.09 _diffrn_measured_fraction_theta_full 0.921 _reflns_number_total 1836 _reflns_number_gt 1170 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008) and SORTX (McArdle, 1995)' _computing_molecular_graphics 'PLATON (Spek, 2009)' _computing_publication_material SHELXL97 _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 'w=1/[\s^2^(Fo^2^)+(0.0463P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.011(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1836 _refine_ls_number_parameters 151 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0623 _refine_ls_R_factor_gt 0.0342 _refine_ls_wR_factor_ref 0.0827 _refine_ls_wR_factor_gt 0.0774 _refine_ls_goodness_of_fit_ref 0.896 _refine_ls_restrained_S_all 0.896 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.105 _refine_diff_density_min -0.086 _refine_diff_density_rms 0.023 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.08983(15) 0.26913(10) 0.42998(7) 0.0721(4) Uani 1 1 d . . . N1 N 0.21952(17) 0.43335(12) 0.52566(10) 0.0519(4) Uani 1 1 d . . . H1 H 0.2694(19) 0.4580(15) 0.5886(11) 0.069(5) Uiso 1 1 d . . . C1 C 0.15085(19) 0.31384(15) 0.51195(11) 0.0494(4) Uani 1 1 d . . . C11 C 0.2394(2) 0.52525(15) 0.45071(11) 0.0496(4) Uani 1 1 d . . . C12 C 0.1544(2) 0.51931(15) 0.35271(11) 0.0553(4) Uani 1 1 d . . . H12 H 0.0794 0.4523 0.3335 0.066 Uiso 1 1 calc R . . C13 C 0.1795(2) 0.61209(16) 0.28247(11) 0.0615(5) Uani 1 1 d . . . C14 C 0.2900(3) 0.71122(18) 0.31279(15) 0.0741(6) Uani 1 1 d . . . H14 H 0.3083 0.7740 0.2668 0.089 Uiso 1 1 calc R . . C15 C 0.3734(3) 0.71818(17) 0.41030(15) 0.0771(6) Uani 1 1 d . . . H15 H 0.4463 0.7864 0.4297 0.093 Uiso 1 1 calc R . . C17 C 0.0864(3) 0.60275(18) 0.17595(12) 0.0873(7) Uani 1 1 d . . . H17A H 0.0314 0.5201 0.1661 0.131 Uiso 0.50 1 calc PR . . H17B H 0.1616 0.6106 0.1305 0.131 Uiso 0.50 1 calc PR . . H17C H 0.0068 0.6716 0.1634 0.131 Uiso 0.50 1 calc PR . . H17D H 0.1018 0.6814 0.1406 0.131 Uiso 0.50 1 calc PR . . H17E H -0.0284 0.5910 0.1762 0.131 Uiso 0.50 1 calc PR . . H17F H 0.1264 0.5299 0.1433 0.131 Uiso 0.50 1 calc PR . . C16 C 0.3503(2) 0.62550(15) 0.47958(12) 0.0631(5) Uani 1 1 d . . . H16 H 0.4087 0.6301 0.5451 0.076 Uiso 1 1 calc R . . C21 C 0.15264(18) 0.23354(13) 0.60459(10) 0.0439(4) Uani 1 1 d . . . C22 C 0.2572(2) 0.25256(14) 0.69480(10) 0.0529(4) Uani 1 1 d . . . H22 H 0.3322 0.3209 0.7027 0.063 Uiso 1 1 calc R . . C23 C 0.2499(2) 0.16933(16) 0.77348(11) 0.0589(5) Uani 1 1 d . . . H23 H 0.3209 0.1847 0.8341 0.071 Uiso 1 1 calc R . . N24 N 0.14827(19) 0.06881(13) 0.76853(9) 0.0614(4) Uani 1 1 d . . . C25 C 0.0480(2) 0.05196(16) 0.68106(12) 0.0707(5) Uani 1 1 d . . . H25 H -0.0253 -0.0175 0.6750 0.085 Uiso 1 1 calc R . . C26 C 0.0454(2) 0.13043(15) 0.59863(11) 0.0611(5) Uani 1 1 d . . . H26 H -0.0285 0.1139 0.5393 0.073 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 O1 0.1100(10) 0.0573(7) 0.0432(7) 0.0010(5) -0.0004(6) -0.0140(7) N1 0.0727(10) 0.0430(8) 0.0403(8) -0.0001(6) 0.0118(7) -0.0050(7) C1 0.0616(11) 0.0452(10) 0.0415(9) -0.0012(8) 0.0096(8) 0.0029(8) C11 0.0661(11) 0.0425(9) 0.0442(9) 0.0029(7) 0.0210(8) 0.0063(8) C12 0.0689(12) 0.0485(9) 0.0516(9) 0.0044(8) 0.0194(8) 0.0085(8) C13 0.0807(14) 0.0567(11) 0.0526(10) 0.0121(9) 0.0272(9) 0.0212(10) C14 0.1029(16) 0.0563(12) 0.0720(13) 0.0205(9) 0.0389(11) 0.0057(11) C15 0.0986(15) 0.0600(12) 0.0796(14) 0.0059(10) 0.0344(11) -0.0134(11) C17 0.1166(17) 0.0866(14) 0.0600(12) 0.0254(10) 0.0203(11) 0.0253(12) C16 0.0807(14) 0.0534(10) 0.0587(10) 0.0018(9) 0.0222(9) -0.0066(10) C21 0.0521(10) 0.0384(9) 0.0413(8) -0.0016(6) 0.0093(7) 0.0038(7) C22 0.0641(11) 0.0457(9) 0.0468(9) 0.0006(7) 0.0052(8) -0.0057(8) C23 0.0740(12) 0.0536(10) 0.0446(9) 0.0013(8) 0.0002(8) 0.0009(10) N24 0.0812(10) 0.0491(9) 0.0518(9) 0.0069(6) 0.0073(7) -0.0040(8) C25 0.0840(14) 0.0604(11) 0.0627(11) 0.0105(9) 0.0012(10) -0.0201(10) C26 0.0730(13) 0.0549(10) 0.0495(10) 0.0054(8) -0.0035(8) -0.0123(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.2209(15) . ? N1 C1 1.3500(18) . ? N1 C11 1.4192(18) . ? N1 H1 0.911(15) . ? C1 C21 1.501(2) . ? C11 C12 1.383(2) . ? C11 C16 1.386(2) . ? C12 C13 1.390(2) . ? C12 H12 0.9300 . ? C13 C14 1.379(2) . ? C13 C17 1.508(2) . ? C14 C15 1.374(2) . ? C14 H14 0.9300 . ? C15 C16 1.376(2) . ? C15 H15 0.9300 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C17 H17D 0.9600 . ? C17 H17E 0.9600 . ? C17 H17F 0.9600 . ? C16 H16 0.9300 . ? C21 C22 1.3736(19) . ? C21 C26 1.3747(19) . ? C22 C23 1.378(2) . ? C22 H22 0.9300 . ? C23 N24 1.3254(19) . ? C23 H23 0.9300 . ? N24 C25 1.3253(17) . ? C25 C26 1.375(2) . ? C25 H25 0.9300 . ? C26 H26 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 C1 N1 C11 127.43(14) . . ? C1 N1 H1 119.1(10) . . ? C11 N1 H1 113.2(10) . . ? O1 C1 N1 123.92(14) . . ? O1 C1 C21 119.58(14) . . ? N1 C1 C21 116.50(13) . . ? C12 C11 C16 119.62(14) . . ? C12 C11 N1 123.56(15) . . ? C16 C11 N1 116.82(14) . . ? C11 C12 C13 120.92(16) . . ? C11 C12 H12 119.5 . . ? C13 C12 H12 119.5 . . ? C14 C13 C12 118.54(16) . . ? C14 C13 C17 121.60(16) . . ? C12 C13 C17 119.85(17) . . ? C15 C14 C13 120.69(16) . . ? C15 C14 H14 119.7 . . ? C13 C14 H14 119.7 . . ? C14 C15 C16 120.85(17) . . ? C14 C15 H15 119.6 . . ? C16 C15 H15 119.6 . . ? C13 C17 H17A 109.5 . . ? C13 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C13 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C13 C17 H17D 109.5 . . ? H17A C17 H17D 141.1 . . ? H17B C17 H17D 56.3 . . ? H17C C17 H17D 56.3 . . ? C13 C17 H17E 109.5 . . ? H17A C17 H17E 56.3 . . ? H17B C17 H17E 141.1 . . ? H17C C17 H17E 56.3 . . ? H17D C17 H17E 109.5 . . ? C13 C17 H17F 109.5 . . ? H17A C17 H17F 56.3 . . ? H17B C17 H17F 56.3 . . ? H17C C17 H17F 141.1 . . ? H17D C17 H17F 109.5 . . ? H17E C17 H17F 109.5 . . ? C15 C16 C11 119.36(16) . . ? C15 C16 H16 120.3 . . ? C11 C16 H16 120.3 . . ? C22 C21 C26 117.00(14) . . ? C22 C21 C1 124.96(14) . . ? C26 C21 C1 118.01(13) . . ? C21 C22 C23 119.32(15) . . ? C21 C22 H22 120.3 . . ? C23 C22 H22 120.3 . . ? N24 C23 C22 124.33(14) . . ? N24 C23 H23 117.8 . . ? C22 C23 H23 117.8 . . ? C25 N24 C23 115.59(14) . . ? N24 C25 C26 124.26(16) . . ? N24 C25 H25 117.9 . . ? C26 C25 H25 117.9 . . ? C21 C26 C25 119.50(14) . . ? C21 C26 H26 120.3 . . ? C25 C26 H26 120.3 . . ? 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 C1 O1 -2.5(3) . . . . ? C11 N1 C1 C21 177.18(14) . . . . ? C1 N1 C11 C12 16.9(2) . . . . ? C1 N1 C11 C16 -163.30(15) . . . . ? C16 C11 C12 C13 0.4(2) . . . . ? N1 C11 C12 C13 -179.79(15) . . . . ? C11 C12 C13 C14 -0.6(2) . . . . ? C11 C12 C13 C17 179.50(14) . . . . ? C12 C13 C14 C15 0.0(3) . . . . ? C17 C13 C14 C15 179.82(16) . . . . ? C13 C14 C15 C16 0.9(3) . . . . ? C14 C15 C16 C11 -1.1(3) . . . . ? C12 C11 C16 C15 0.5(2) . . . . ? N1 C11 C16 C15 -179.34(15) . . . . ? O1 C1 C21 C22 158.99(15) . . . . ? N1 C1 C21 C22 -20.7(2) . . . . ? O1 C1 C21 C26 -18.9(2) . . . . ? N1 C1 C21 C26 161.42(14) . . . . ? C26 C21 C22 C23 0.0(2) . . . . ? C1 C21 C22 C23 -177.97(15) . . . . ? C21 C22 C23 N24 0.8(3) . . . . ? C22 C23 N24 C25 -0.9(3) . . . . ? C23 N24 C25 C26 0.3(3) . . . . ? C22 C21 C26 C25 -0.5(2) . . . . ? C1 C21 C26 C25 177.60(15) . . . . ? N24 C25 C26 C21 0.4(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # # Hydrogen bonding scheme # ======== ======= ====== # # D H A D-H H...A D...A D-H...A symm publ # - - - --- ----- ----- ------- ---- ---- N1 H1 N24 0.911(15) 2.240(16) 3.1265(18) 164.1(14) 2_556 yes C22 H22 N24 0.93 2.57 3.353(2) 141.7 2_556 yes C12 H12 O1 0.93 2.28 2.8615(19) 119.8 . yes C23 H23 O1 0.93 2.41 3.2538(19) 151.5 4_666 yes #============================================================ data_NpoM_[10-004] _database_code_depnum_ccdc_archive 'CCDC 809620' #TrackingRef 'NxxM_5-Cl-NoxM_fin.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common NpoM _chemical_melting_point 398 _chemical_formula_moiety 'C13 H12 N2 O' _chemical_formula_sum 'C13 H12 N2 O' _chemical_formula_weight 212.25 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 Monoclinic _symmetry_space_group_name_H-M 'C c' _symmetry_space_group_name_Hall 'C -2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 13.0101(6) _cell_length_b 10.4826(3) _cell_length_c 9.7957(4) _cell_angle_alpha 90.00 _cell_angle_beta 122.729(6) _cell_angle_gamma 90.00 _cell_volume 1123.84(11) _cell_formula_units_Z 4 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 4635 _cell_measurement_theta_min 3.9 _cell_measurement_theta_max 27.9 _exptl_crystal_description Block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.47 _exptl_crystal_size_mid 0.43 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.254 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type Analytical _exptl_absorpt_correction_T_min 0.963 _exptl_absorpt_correction_T_max 0.980 _exptl_absorpt_process_details '(ABSFAC, Clark and Reid, 1998)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Xcalibur, Sapphire3, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_standards_number 4666 _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 1 _diffrn_reflns_number 8432 _diffrn_reflns_av_R_equivalents 0.031 _diffrn_reflns_av_sigmaI/netI 0.018 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.89 _diffrn_reflns_theta_max 27.90 _diffrn_measured_fraction_theta_max 0.960 _diffrn_reflns_theta_full 27.90 _diffrn_measured_fraction_theta_full 0.997 _reflns_number_total 1285 _reflns_number_gt 1109 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008) and SORTX (McArdle, 1995)' _computing_molecular_graphics 'PLATON (Spek, 2009)' _computing_publication_material SHELXL97 _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 'w=1/[\s^2^(Fo^2^)+(0.058P)^2^] 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, 1983)' #_refine_ls_abs_structure_Flack 0.1(15) _refine_ls_number_reflns 1285 _refine_ls_number_parameters 150 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0360 _refine_ls_R_factor_gt 0.0300 _refine_ls_wR_factor_ref 0.0805 _refine_ls_wR_factor_gt 0.0785 _refine_ls_goodness_of_fit_ref 0.993 _refine_ls_restrained_S_all 0.992 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.139 _refine_diff_density_min -0.106 _refine_diff_density_rms 0.025 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.05790(13) 0.03910(14) 0.95428(15) 0.0543(4) Uani 1 1 d . . . N1 N 0.01155(15) 0.00315(17) 0.70109(19) 0.0481(4) Uani 1 1 d . . . H1 H 0.031(2) -0.026(2) 0.642(3) 0.062(7) Uiso 1 1 d . . . C1 C 0.08439(15) -0.00667(16) 0.86165(19) 0.0387(4) Uani 1 1 d . . . C11 C -0.10853(16) 0.05522(19) 0.6214(2) 0.0457(4) Uani 1 1 d . . . C12 C -0.13710(18) 0.16595(19) 0.5300(2) 0.0505(4) Uani 1 1 d . . . C13 C -0.25713(19) 0.2101(2) 0.4528(3) 0.0637(6) Uani 1 1 d . . . H13 H -0.2791 0.2830 0.3888 0.076 Uiso 1 1 calc R . . C14 C -0.3437(2) 0.1497(3) 0.4682(3) 0.0718(7) Uani 1 1 d . . . H14 H -0.4227 0.1820 0.4164 0.086 Uiso 1 1 calc R . . C15 C -0.3131(2) 0.0419(3) 0.5601(3) 0.0704(7) Uani 1 1 d . . . H15 H -0.3713 0.0011 0.5721 0.084 Uiso 1 1 calc R . . C16 C -0.1965(2) -0.0071(2) 0.6354(3) 0.0581(5) Uani 1 1 d . . . H16 H -0.1767 -0.0819 0.6956 0.070 Uiso 1 1 calc R . . C17 C -0.0440(2) 0.2394(2) 0.5172(3) 0.0646(5) Uani 1 1 d . . . H17A H 0.0285 0.2498 0.6233 0.097 Uiso 0.50 1 calc PR . . H17B H -0.0764 0.3217 0.4708 0.097 Uiso 0.50 1 calc PR . . H17C H -0.0243 0.1937 0.4493 0.097 Uiso 0.50 1 calc PR . . H17D H -0.0766 0.2603 0.4056 0.097 Uiso 0.50 1 calc PR . . H17E H 0.0283 0.1885 0.5582 0.097 Uiso 0.50 1 calc PR . . H17F H -0.0239 0.3164 0.5797 0.097 Uiso 0.50 1 calc PR . . C21 C 0.20365(16) -0.07465(17) 0.92612(19) 0.0415(4) Uani 1 1 d . . . C22 C 0.21928(16) -0.17120(18) 0.8430(2) 0.0484(4) Uani 1 1 d . . . H22 H 0.1547 -0.1976 0.7418 0.058 Uiso 1 1 calc R . . C23 C 0.33303(19) -0.2279(2) 0.9133(3) 0.0594(5) Uani 1 1 d . . . H23 H 0.3422 -0.2935 0.8568 0.071 Uiso 1 1 calc R . . N24 N 0.42993(16) -0.19481(19) 1.0563(2) 0.0623(5) Uani 1 1 d . . . C25 C 0.41318(19) -0.1021(2) 1.1354(2) 0.0616(6) Uani 1 1 d . . . H25 H 0.4797 -0.0772 1.2359 0.074 Uiso 1 1 calc R . . C26 C 0.30318(18) -0.0405(2) 1.0775(2) 0.0535(5) Uani 1 1 d . . . H26 H 0.2959 0.0225 1.1386 0.064 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 O1 0.0546(8) 0.0762(9) 0.0420(7) -0.0058(6) 0.0326(6) 0.0003(7) N1 0.0468(8) 0.0664(10) 0.0362(7) 0.0037(7) 0.0259(7) 0.0122(7) C1 0.0413(9) 0.0431(9) 0.0355(8) 0.0003(6) 0.0232(7) -0.0048(7) C11 0.0434(10) 0.0561(11) 0.0358(8) -0.0044(7) 0.0203(8) 0.0061(8) C12 0.0506(10) 0.0508(10) 0.0427(9) -0.0071(8) 0.0203(8) 0.0034(8) C13 0.0570(13) 0.0596(12) 0.0568(12) -0.0024(9) 0.0192(10) 0.0146(10) C14 0.0439(11) 0.0858(17) 0.0687(14) -0.0126(13) 0.0192(11) 0.0125(11) C15 0.0489(12) 0.0915(18) 0.0707(15) -0.0099(14) 0.0323(12) -0.0026(11) C16 0.0547(12) 0.0679(13) 0.0551(12) 0.0002(10) 0.0320(10) 0.0019(10) C17 0.0671(13) 0.0602(12) 0.0626(12) 0.0012(10) 0.0325(11) 0.0013(10) C21 0.0429(9) 0.0475(9) 0.0358(8) 0.0049(7) 0.0224(7) -0.0019(7) C22 0.0437(9) 0.0536(11) 0.0411(8) -0.0032(8) 0.0185(8) 0.0008(8) C23 0.0527(12) 0.0636(12) 0.0568(11) -0.0018(10) 0.0262(10) 0.0065(10) N24 0.0434(9) 0.0729(12) 0.0582(10) 0.0060(9) 0.0193(8) 0.0062(9) C25 0.0436(10) 0.0758(15) 0.0435(10) -0.0003(10) 0.0091(8) -0.0050(10) C26 0.0518(12) 0.0603(12) 0.0403(9) -0.0051(8) 0.0196(9) -0.0035(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.229(2) . ? N1 C1 1.331(2) . ? N1 C11 1.425(2) . ? N1 H1 0.80(3) . ? C1 C21 1.501(2) . ? C11 C16 1.387(3) . ? C11 C12 1.388(3) . ? C12 C13 1.396(3) . ? C12 C17 1.496(3) . ? C13 C14 1.369(3) . ? C13 H13 0.9300 . ? C14 C15 1.363(4) . ? C14 H14 0.9300 . ? C15 C16 1.378(3) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C17 H17D 0.9600 . ? C17 H17E 0.9600 . ? C17 H17F 0.9600 . ? C21 C22 1.381(2) . ? C21 C26 1.388(3) . ? C22 C23 1.384(3) . ? C22 H22 0.9300 . ? C23 N24 1.327(3) . ? C23 H23 0.9300 . ? N24 C25 1.333(3) . ? C25 C26 1.381(3) . ? C25 H25 0.9300 . ? C26 H26 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 C1 N1 C11 123.13(15) . . ? C1 N1 H1 121.3(18) . . ? C11 N1 H1 115.3(18) . . ? O1 C1 N1 122.53(16) . . ? O1 C1 C21 120.88(15) . . ? N1 C1 C21 116.58(14) . . ? C16 C11 C12 120.67(19) . . ? C16 C11 N1 118.95(19) . . ? C12 C11 N1 120.38(18) . . ? C11 C12 C13 117.2(2) . . ? C11 C12 C17 122.51(18) . . ? C13 C12 C17 120.22(19) . . ? C14 C13 C12 122.2(2) . . ? C14 C13 H13 118.9 . . ? C12 C13 H13 118.9 . . ? C15 C14 C13 119.5(2) . . ? C15 C14 H14 120.2 . . ? C13 C14 H14 120.2 . . ? C14 C15 C16 120.4(2) . . ? C14 C15 H15 119.8 . . ? C16 C15 H15 119.8 . . ? C15 C16 C11 120.0(2) . . ? C15 C16 H16 120.0 . . ? C11 C16 H16 120.0 . . ? C12 C17 H17A 109.5 . . ? C12 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C12 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C12 C17 H17D 109.5 . . ? H17A C17 H17D 141.1 . . ? H17B C17 H17D 56.3 . . ? H17C C17 H17D 56.3 . . ? C12 C17 H17E 109.5 . . ? H17A C17 H17E 56.3 . . ? H17B C17 H17E 141.1 . . ? H17C C17 H17E 56.3 . . ? H17D C17 H17E 109.5 . . ? C12 C17 H17F 109.5 . . ? H17A C17 H17F 56.3 . . ? H17B C17 H17F 56.3 . . ? H17C C17 H17F 141.1 . . ? H17D C17 H17F 109.5 . . ? H17E C17 H17F 109.5 . . ? C22 C21 C26 117.96(17) . . ? C22 C21 C1 123.22(15) . . ? C26 C21 C1 118.82(16) . . ? C21 C22 C23 118.69(17) . . ? C21 C22 H22 120.7 . . ? C23 C22 H22 120.7 . . ? N24 C23 C22 124.2(2) . . ? N24 C23 H23 117.9 . . ? C22 C23 H23 117.9 . . ? C23 N24 C25 116.34(18) . . ? N24 C25 C26 124.09(18) . . ? N24 C25 H25 118.0 . . ? C26 C25 H25 118.0 . . ? C25 C26 C21 118.65(19) . . ? C25 C26 H26 120.7 . . ? C21 C26 H26 120.7 . . ? 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 C1 O1 -6.8(3) . . . . ? C11 N1 C1 C21 174.53(17) . . . . ? C1 N1 C11 C16 -64.1(3) . . . . ? C1 N1 C11 C12 116.4(2) . . . . ? C16 C11 C12 C13 -0.6(3) . . . . ? N1 C11 C12 C13 178.81(17) . . . . ? C16 C11 C12 C17 177.34(19) . . . . ? N1 C11 C12 C17 -3.3(3) . . . . ? C11 C12 C13 C14 1.5(3) . . . . ? C17 C12 C13 C14 -176.5(2) . . . . ? C12 C13 C14 C15 -0.8(3) . . . . ? C13 C14 C15 C16 -0.8(3) . . . . ? C14 C15 C16 C11 1.7(3) . . . . ? C12 C11 C16 C15 -1.0(3) . . . . ? N1 C11 C16 C15 179.62(18) . . . . ? O1 C1 C21 C22 151.25(17) . . . . ? N1 C1 C21 C22 -30.1(2) . . . . ? O1 C1 C21 C26 -27.9(2) . . . . ? N1 C1 C21 C26 150.77(17) . . . . ? C26 C21 C22 C23 -0.7(3) . . . . ? C1 C21 C22 C23 -179.89(17) . . . . ? C21 C22 C23 N24 -0.7(3) . . . . ? C22 C23 N24 C25 1.1(3) . . . . ? C23 N24 C25 C26 0.0(3) . . . . ? N24 C25 C26 C21 -1.3(3) . . . . ? C22 C21 C26 C25 1.7(3) . . . . ? C1 C21 C26 C25 -179.12(17) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # # Hydrogen bonding scheme # ======== ======= ====== # # D H A D-H H...A D...A D-H...A symm publ # - - - --- ----- ----- ------- ---- ---- N1 H1 O1 0.80(3) 2.06(3) 2.825(2) 159(2) 2_554 yes C17 H17E N1 0.96 2.47 2.914(3) 108 . yes C23 H23 Cg1 0.93 2.90 3.713(3) 147 3_545 yes # C23 H23 C11 0.93 3.14 4.034(3) 163 3_545 # C23 H23 C12 0.93 3.38 4.131(3) 139 3_545 # C23 H23 C13 0.93 3.44 4.053(3) 126 3_545 # C23 H23 C14 0.93 3.28 3.886(3) 125 3_545 # C23 H23 C15 0.93 3.03 3.781(3) 139 3_545 # C23 H23 C16 0.93 2.97 3.873(3) 166 3_545 # Cg1 is the C~6~ aromatic ring centroid at site 3_545 [1/2+X,-1/2+Y,Z] #============================================================ data_NmpM_[10-005] _database_code_depnum_ccdc_archive 'CCDC 809621' #TrackingRef 'NxxM_5-Cl-NoxM_fin.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common NmpM _chemical_melting_point 421 _chemical_formula_moiety 'C13 H12 N2 O' _chemical_formula_sum 'C13 H12 N2 O' _chemical_formula_weight 212.25 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 Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 10.5017(5) _cell_length_b 4.8807(2) _cell_length_c 21.3459(9) _cell_angle_alpha 90.00 _cell_angle_beta 100.868(4) _cell_angle_gamma 90.00 _cell_volume 1074.47(8) _cell_formula_units_Z 4 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 2175 _cell_measurement_theta_min 3.8 _cell_measurement_theta_max 26.3 _exptl_crystal_description Needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.67 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.312 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type Analytical _exptl_absorpt_correction_T_min 0.945 _exptl_absorpt_correction_T_max 0.995 _exptl_absorpt_process_details '(ABSFAC, Clark and Reid, 1998)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Xcalibur, Sapphire3, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_standards_number 12031 _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 1 _diffrn_reflns_number 11243 _diffrn_reflns_av_R_equivalents 0.0549 _diffrn_reflns_av_sigmaI/netI 0.0736 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 3.89 _diffrn_reflns_theta_max 26.42 _diffrn_measured_fraction_theta_max 0.940 _diffrn_reflns_theta_full 26.42 _diffrn_measured_fraction_theta_full 0.997 _reflns_number_total 2070 _reflns_number_gt 1001 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008) and SORTX (McArdle, 1995)' _computing_molecular_graphics 'PLATON (Spek, 2009)' _computing_publication_material SHELXL97 _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 'w=1/[\s^2^(Fo^2^)+(0.0318P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0037(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2070 _refine_ls_number_parameters 151 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0993 _refine_ls_R_factor_gt 0.0363 _refine_ls_wR_factor_ref 0.0730 _refine_ls_wR_factor_gt 0.0650 _refine_ls_goodness_of_fit_ref 0.766 _refine_ls_restrained_S_all 0.766 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.122 _refine_diff_density_min -0.097 _refine_diff_density_rms 0.024 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.16004(12) -0.0992(2) 0.45848(6) 0.0667(4) Uani 1 1 d . . . N1 N 0.18543(14) -0.1720(3) 0.35668(7) 0.0450(4) Uani 1 1 d . . . H1 H 0.1600(13) -0.117(3) 0.3171(7) 0.038(5) Uiso 1 1 d . . . C1 C 0.13014(16) -0.0475(3) 0.40150(8) 0.0446(4) Uani 1 1 d . . . C11 C 0.28360(16) -0.3745(3) 0.36561(8) 0.0427(4) Uani 1 1 d . . . C12 C 0.33448(17) -0.4908(3) 0.42379(8) 0.0549(5) Uani 1 1 d . . . H12 H 0.3038 -0.4386 0.4601 0.066 Uiso 1 1 calc R . . C13 C 0.43170(18) -0.6863(4) 0.42782(9) 0.0595(5) Uani 1 1 d . . . H13 H 0.4645 -0.7639 0.4674 0.071 Uiso 1 1 calc R . . C14 C 0.48134(17) -0.7696(3) 0.37609(9) 0.0521(5) Uani 1 1 d . . . C15 C 0.42777(17) -0.6541(4) 0.31823(9) 0.0612(5) Uani 1 1 d . . . H15 H 0.4575 -0.7086 0.2818 0.073 Uiso 1 1 calc R . . C16 C 0.33098(18) -0.4593(4) 0.31301(8) 0.0571(5) Uani 1 1 d . . . H16 H 0.2973 -0.3843 0.2733 0.069 Uiso 1 1 calc R . . C17 C 0.58778(17) -0.9794(3) 0.38248(10) 0.0716(6) Uani 1 1 d . . . H17A H 0.5938 -1.0486 0.3410 0.107 Uiso 0.50 1 calc PR . . H17B H 0.5689 -1.1274 0.4089 0.107 Uiso 0.50 1 calc PR . . H17C H 0.6686 -0.8961 0.4016 0.107 Uiso 0.50 1 calc PR . . H17D H 0.6271 -0.9995 0.4266 0.107 Uiso 0.50 1 calc PR . . H17E H 0.6520 -0.9207 0.3588 0.107 Uiso 0.50 1 calc PR . . H17F H 0.5523 -1.1520 0.3661 0.107 Uiso 0.50 1 calc PR . . C21 C 0.02659(15) 0.1595(3) 0.37868(8) 0.0394(4) Uani 1 1 d . . . C22 C -0.01596(17) 0.2317(4) 0.31591(8) 0.0533(5) Uani 1 1 d . . . H22 H 0.0236 0.1480 0.2854 0.064 Uiso 1 1 calc R . . N23 N -0.10977(14) 0.4129(3) 0.29553(6) 0.0562(4) Uani 1 1 d . . . C24 C -0.16437(18) 0.5319(4) 0.33984(9) 0.0545(5) Uani 1 1 d . . . H24 H -0.2297 0.6598 0.3270 0.065 Uiso 1 1 calc R . . C25 C -0.12915(19) 0.4754(4) 0.40328(9) 0.0631(5) Uani 1 1 d . . . H25 H -0.1695 0.5637 0.4329 0.076 Uiso 1 1 calc R . . C26 C -0.03327(17) 0.2864(4) 0.42275(8) 0.0560(5) Uani 1 1 d . . . H26 H -0.0087 0.2442 0.4658 0.067 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 O1 0.0767(10) 0.0872(10) 0.0371(8) 0.0113(7) 0.0130(6) 0.0230(8) N1 0.0495(10) 0.0509(10) 0.0335(9) 0.0016(8) 0.0047(8) 0.0038(8) C1 0.0451(11) 0.0514(11) 0.0379(11) 0.0014(9) 0.0091(9) -0.0033(9) C11 0.0415(11) 0.0430(10) 0.0421(11) -0.0016(9) 0.0041(8) -0.0017(9) C12 0.0572(13) 0.0617(13) 0.0455(11) 0.0021(9) 0.0087(9) 0.0063(11) C13 0.0581(13) 0.0609(13) 0.0562(13) 0.0066(10) 0.0025(10) 0.0062(11) C14 0.0445(12) 0.0440(12) 0.0656(13) -0.0051(10) 0.0053(10) -0.0015(9) C15 0.0626(14) 0.0648(14) 0.0576(13) -0.0103(11) 0.0151(10) 0.0089(11) C16 0.0620(13) 0.0647(13) 0.0437(11) 0.0000(10) 0.0076(10) 0.0107(11) C17 0.0561(13) 0.0566(13) 0.0998(17) -0.0058(11) 0.0089(11) 0.0061(11) C21 0.0405(10) 0.0441(11) 0.0344(10) 0.0005(8) 0.0090(8) -0.0046(9) C22 0.0570(12) 0.0631(13) 0.0418(11) -0.0020(10) 0.0146(9) 0.0112(11) N23 0.0564(11) 0.0658(11) 0.0454(9) 0.0025(8) 0.0074(8) 0.0134(9) C24 0.0476(12) 0.0561(12) 0.0603(13) 0.0041(10) 0.0117(10) 0.0073(9) C25 0.0720(14) 0.0721(14) 0.0491(12) 0.0019(11) 0.0216(11) 0.0179(12) C26 0.0640(13) 0.0677(13) 0.0379(11) 0.0044(10) 0.0138(10) 0.0062(11) _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 C1 1.2238(17) . ? N1 C1 1.353(2) . ? N1 C11 1.415(2) . ? N1 H1 0.879(14) . ? C1 C21 1.497(2) . ? C11 C16 1.375(2) . ? C11 C12 1.378(2) . ? C12 C13 1.388(2) . ? C12 H12 0.9300 . ? C13 C14 1.369(2) . ? C13 H13 0.9300 . ? C14 C15 1.378(2) . ? C14 C17 1.503(2) . ? C15 C16 1.381(2) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C17 H17D 0.9600 . ? C17 H17E 0.9600 . ? C17 H17F 0.9600 . ? C21 C26 1.374(2) . ? C21 C22 1.376(2) . ? C22 N23 1.3344(19) . ? C22 H22 0.9300 . ? N23 C24 1.329(2) . ? C24 C25 1.363(2) . ? C24 H24 0.9300 . ? C25 C26 1.371(2) . ? C25 H25 0.9300 . ? C26 H26 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 C1 N1 C11 128.12(15) . . ? C1 N1 H1 116.7(9) . . ? C11 N1 H1 115.2(9) . . ? O1 C1 N1 123.10(16) . . ? O1 C1 C21 119.81(15) . . ? N1 C1 C21 117.08(15) . . ? C16 C11 C12 118.26(17) . . ? C16 C11 N1 117.83(16) . . ? C12 C11 N1 123.91(16) . . ? C11 C12 C13 119.65(17) . . ? C11 C12 H12 120.2 . . ? C13 C12 H12 120.2 . . ? C14 C13 C12 122.80(18) . . ? C14 C13 H13 118.6 . . ? C12 C13 H13 118.6 . . ? C13 C14 C15 116.63(18) . . ? C13 C14 C17 121.27(18) . . ? C15 C14 C17 122.10(18) . . ? C14 C15 C16 121.62(18) . . ? C14 C15 H15 119.2 . . ? C16 C15 H15 119.2 . . ? C11 C16 C15 121.03(17) . . ? C11 C16 H16 119.5 . . ? C15 C16 H16 119.5 . . ? C14 C17 H17A 109.5 . . ? C14 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C14 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C14 C17 H17D 109.5 . . ? H17A C17 H17D 141.1 . . ? H17B C17 H17D 56.3 . . ? H17C C17 H17D 56.3 . . ? C14 C17 H17E 109.5 . . ? H17A C17 H17E 56.3 . . ? H17B C17 H17E 141.1 . . ? H17C C17 H17E 56.3 . . ? H17D C17 H17E 109.5 . . ? C14 C17 H17F 109.5 . . ? H17A C17 H17F 56.3 . . ? H17B C17 H17F 56.3 . . ? H17C C17 H17F 141.1 . . ? H17D C17 H17F 109.5 . . ? H17E C17 H17F 109.5 . . ? C26 C21 C22 116.41(16) . . ? C26 C21 C1 118.67(15) . . ? C22 C21 C1 124.91(15) . . ? N23 C22 C21 124.85(16) . . ? N23 C22 H22 117.6 . . ? C21 C22 H22 117.6 . . ? C24 N23 C22 116.67(15) . . ? N23 C24 C25 123.11(17) . . ? N23 C24 H24 118.4 . . ? C25 C24 H24 118.4 . . ? C24 C25 C26 118.90(18) . . ? C24 C25 H25 120.5 . . ? C26 C25 H25 120.5 . . ? C25 C26 C21 120.05(16) . . ? C25 C26 H26 120.0 . . ? C21 C26 H26 120.0 . . ? 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 C1 O1 -0.3(3) . . . . ? C11 N1 C1 C21 -179.42(14) . . . . ? C1 N1 C11 C16 -175.89(17) . . . . ? C1 N1 C11 C12 3.9(3) . . . . ? C16 C11 C12 C13 0.5(2) . . . . ? N1 C11 C12 C13 -179.32(15) . . . . ? C11 C12 C13 C14 0.5(3) . . . . ? C12 C13 C14 C15 -1.5(3) . . . . ? C12 C13 C14 C17 179.24(15) . . . . ? C13 C14 C15 C16 1.5(3) . . . . ? C17 C14 C15 C16 -179.28(16) . . . . ? C12 C11 C16 C15 -0.5(3) . . . . ? N1 C11 C16 C15 179.31(15) . . . . ? C14 C15 C16 C11 -0.5(3) . . . . ? O1 C1 C21 C26 -0.3(2) . . . . ? N1 C1 C21 C26 178.87(16) . . . . ? O1 C1 C21 C22 -179.23(16) . . . . ? N1 C1 C21 C22 -0.1(2) . . . . ? C26 C21 C22 N23 -0.1(3) . . . . ? C1 C21 C22 N23 178.83(16) . . . . ? C21 C22 N23 C24 0.5(3) . . . . ? C22 N23 C24 C25 -0.3(3) . . . . ? N23 C24 C25 C26 -0.3(3) . . . . ? C24 C25 C26 C21 0.7(3) . . . . ? C22 C21 C26 C25 -0.5(2) . . . . ? C1 C21 C26 C25 -179.51(15) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # # Hydrogen bonding scheme # ======== ======= ====== # # D H A D-H H...A D...A D-H...A symm publ # - - - --- ----- ----- ------- ---- ---- N1 H1 N23 0.879(14) 2.367(14) 3.223(2) 164.7(12) 2_545 yes C12 H12 O1 0.93 2.24 2.841(2) 122 . yes C22 H22 N1 0.93 2.58 2.901(2) 101 . yes C22 H22 N23 0.93 2.39 3.318(2) 176 2_545 yes C26 H26 O1 0.93 2.57 3.210(2) 126 3_556 yes #============================================================ data_NmmM_[10-006] _database_code_depnum_ccdc_archive 'CCDC 809622' #TrackingRef 'NxxM_5-Cl-NoxM_fin.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common NmmM _chemical_melting_point 387 _chemical_formula_moiety 'C13 H12 N2 O' _chemical_formula_sum 'C13 H12 N2 O' _chemical_formula_weight 212.25 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 Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.3767(4) _cell_length_b 9.9187(3) _cell_length_c 12.3386(4) _cell_angle_alpha 86.958(3) _cell_angle_beta 86.980(3) _cell_angle_gamma 71.410(3) _cell_volume 1085.36(7) _cell_formula_units_Z 4 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 11494 _cell_measurement_theta_min 3.6 _cell_measurement_theta_max 31.5 _exptl_crystal_description Block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.299 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type Analytical _exptl_absorpt_correction_T_min 0.964 _exptl_absorpt_correction_T_max 0.985 _exptl_absorpt_process_details '(ABSFAC, Clark and Reid, 1998)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Xcalibur, Sapphire3, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_standards_number 26646 _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 1 _diffrn_reflns_number 26207 _diffrn_reflns_av_R_equivalents 0.0255 _diffrn_reflns_av_sigmaI/netI 0.0284 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.62 _diffrn_reflns_theta_max 31.56 _diffrn_measured_fraction_theta_max 0.961 _diffrn_reflns_theta_full 31.56 _diffrn_measured_fraction_theta_full 0.998 _reflns_number_total 6987 _reflns_number_gt 4966 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008) and SORTX (McArdle, 1995)' _computing_molecular_graphics 'PLATON (Spek, 2009)' _computing_publication_material SHELXL97 _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 'w=1/[\s^2^(Fo^2^)+(0.0712P)^2^+0.4747P] 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 6987 _refine_ls_number_parameters 299 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0754 _refine_ls_R_factor_gt 0.0565 _refine_ls_wR_factor_ref 0.1789 _refine_ls_wR_factor_gt 0.1735 _refine_ls_goodness_of_fit_ref 1.094 _refine_ls_restrained_S_all 1.094 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.285 _refine_diff_density_min -0.239 _refine_diff_density_rms 0.048 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 O1A O 0.08761(18) 0.16532(17) -0.00760(11) 0.0600(5) Uani 1 1 d . . . C1A C 0.16674(19) 0.08378(18) -0.07310(13) 0.0350(4) Uani 1 1 d . . . N1A N 0.26234(18) -0.04707(15) -0.04749(11) 0.0357(3) Uani 1 1 d . . . H1A H 0.312(3) -0.104(2) -0.1026(19) 0.049(6) Uiso 1 1 d . . . C11A C 0.29092(18) -0.11337(18) 0.05722(13) 0.0322(3) Uani 1 1 d . . . C12A C 0.2702(2) -0.03757(19) 0.15161(13) 0.0364(4) Uani 1 1 d . . . H12A H 0.2274 0.0609 0.1484 0.044 Uiso 1 1 calc R . . C13A C 0.3136(2) -0.1090(2) 0.25119(14) 0.0391(4) Uani 1 1 d . . . C14A C 0.3749(2) -0.2560(2) 0.25548(16) 0.0456(5) Uani 1 1 d . . . H14A H 0.4048 -0.3042 0.3213 0.055 Uiso 1 1 calc R . . C15A C 0.3914(2) -0.3308(2) 0.16198(17) 0.0454(4) Uani 1 1 d . . . H15A H 0.4307 -0.4296 0.1657 0.054 Uiso 1 1 calc R . . C16A C 0.3505(2) -0.26109(19) 0.06284(15) 0.0381(4) Uani 1 1 d . . . H16A H 0.3627 -0.3126 0.0003 0.046 Uiso 1 1 calc R . . C17A C 0.2946(3) -0.0253(3) 0.35246(16) 0.0572(6) Uani 1 1 d . . . H17A H 0.3698 -0.0760 0.4028 0.086 Uiso 0.50 1 calc PR . . H17B H 0.1963 -0.0129 0.3852 0.086 Uiso 0.50 1 calc PR . . H17C H 0.3056 0.0661 0.3339 0.086 Uiso 0.50 1 calc PR . . H17D H 0.2113 0.0608 0.3451 0.086 Uiso 0.50 1 calc PR . . H17E H 0.3848 -0.0022 0.3627 0.086 Uiso 0.50 1 calc PR . . H17F H 0.2755 -0.0813 0.4140 0.086 Uiso 0.50 1 calc PR . . C21A C 0.16440(19) 0.12420(17) -0.19224(12) 0.0305(3) Uani 1 1 d . . . C22A C 0.02933(19) 0.20978(19) -0.23484(13) 0.0356(4) Uani 1 1 d . . . H22A H -0.0550 0.2387 -0.1881 0.043 Uiso 1 1 calc R . . N23A N 0.01460(18) 0.25249(17) -0.33948(12) 0.0407(3) Uani 1 1 d . . . C24A C 0.1376(2) 0.2100(2) -0.40465(14) 0.0411(4) Uani 1 1 d . . . H24A H 0.1290 0.2380 -0.4778 0.049 Uiso 1 1 calc R . . C25A C 0.2763(2) 0.1273(2) -0.36967(15) 0.0429(4) Uani 1 1 d . . . H25A H 0.3592 0.1013 -0.4179 0.051 Uiso 1 1 calc R . . C26A C 0.2901(2) 0.08341(19) -0.26149(14) 0.0382(4) Uani 1 1 d . . . H26A H 0.3825 0.0273 -0.2357 0.046 Uiso 1 1 calc R . . O1B O 0.43600(15) 0.35216(15) 0.51592(10) 0.0462(3) Uani 1 1 d . . . C1B C 0.34111(18) 0.42279(17) 0.45405(12) 0.0307(3) Uani 1 1 d . . . N1B N 0.22938(17) 0.54310(16) 0.48076(11) 0.0350(3) Uani 1 1 d . . . H1B H 0.176(2) 0.598(2) 0.4274(18) 0.042(6) Uiso 1 1 d . . . C11B C 0.20190(18) 0.60329(18) 0.58457(13) 0.0317(3) Uani 1 1 d . . . C12B C 0.2226(2) 0.5203(2) 0.68050(13) 0.0356(4) Uani 1 1 d . . . H12B H 0.2635 0.4218 0.6779 0.043 Uiso 1 1 calc R . . C13B C 0.1824(2) 0.5840(2) 0.78068(14) 0.0392(4) Uani 1 1 d . . . C14B C 0.1244(2) 0.7309(2) 0.78349(16) 0.0451(5) Uani 1 1 d . . . H14B H 0.0977 0.7743 0.8498 0.054 Uiso 1 1 calc R . . C15B C 0.1059(2) 0.8135(2) 0.68799(17) 0.0453(4) Uani 1 1 d . . . H15B H 0.0675 0.9121 0.6908 0.054 Uiso 1 1 calc R . . C16B C 0.1441(2) 0.75066(19) 0.58812(15) 0.0384(4) Uani 1 1 d . . . H16B H 0.1311 0.8066 0.5242 0.046 Uiso 1 1 calc R . . C17B C 0.1998(3) 0.4927(3) 0.88404(16) 0.0582(6) Uani 1 1 d . . . H17G H 0.2414 0.3942 0.8669 0.087 Uiso 0.50 1 calc PR . . H17H H 0.1031 0.5086 0.9204 0.087 Uiso 0.50 1 calc PR . . H17I H 0.2660 0.5171 0.9306 0.087 Uiso 0.50 1 calc PR . . H17J H 0.1656 0.5524 0.9451 0.087 Uiso 0.50 1 calc PR . . H17K H 0.3039 0.4380 0.8915 0.087 Uiso 0.50 1 calc PR . . H17L H 0.1411 0.4295 0.8813 0.087 Uiso 0.50 1 calc PR . . C21B C 0.34038(18) 0.37857(16) 0.33955(12) 0.0287(3) Uani 1 1 d . . . C22B C 0.47763(19) 0.29986(18) 0.29173(13) 0.0338(3) Uani 1 1 d . . . H22B H 0.5638 0.2801 0.3316 0.041 Uiso 1 1 calc R . . N23B N 0.49164(17) 0.25132(16) 0.19133(12) 0.0380(3) Uani 1 1 d . . . C24B C 0.3664(2) 0.2804(2) 0.13560(14) 0.0386(4) Uani 1 1 d . . . H24B H 0.3747 0.2481 0.0654 0.046 Uiso 1 1 calc R . . C25B C 0.2254(2) 0.3559(2) 0.17659(14) 0.0400(4) Uani 1 1 d . . . H25B H 0.1410 0.3724 0.1352 0.048 Uiso 1 1 calc R . . C26B C 0.21175(19) 0.40644(19) 0.28016(14) 0.0357(4) Uani 1 1 d . . . H26B H 0.1181 0.4582 0.3095 0.043 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 O1A 0.0642(10) 0.0573(9) 0.0314(7) -0.0059(6) 0.0025(6) 0.0187(7) C1A 0.0361(8) 0.0374(8) 0.0244(7) -0.0012(6) -0.0015(6) -0.0015(7) N1A 0.0442(8) 0.0314(7) 0.0243(6) -0.0009(5) -0.0003(6) -0.0019(6) C11A 0.0316(8) 0.0348(8) 0.0273(7) 0.0040(6) -0.0015(6) -0.0071(6) C12A 0.0408(9) 0.0374(9) 0.0292(8) 0.0010(6) -0.0040(6) -0.0097(7) C13A 0.0345(8) 0.0558(11) 0.0275(8) 0.0044(7) -0.0046(6) -0.0152(8) C14A 0.0407(10) 0.0560(12) 0.0361(9) 0.0177(8) -0.0078(7) -0.0118(8) C15A 0.0437(10) 0.0363(9) 0.0493(11) 0.0129(8) -0.0002(8) -0.0057(8) C16A 0.0391(9) 0.0351(9) 0.0366(9) 0.0010(7) 0.0019(7) -0.0075(7) C17A 0.0581(13) 0.0807(16) 0.0304(9) -0.0018(9) -0.0074(9) -0.0178(12) C21A 0.0352(8) 0.0282(7) 0.0243(7) -0.0012(5) -0.0032(6) -0.0045(6) C22A 0.0334(8) 0.0377(9) 0.0300(8) -0.0019(6) -0.0013(6) -0.0031(7) N23A 0.0380(8) 0.0459(9) 0.0317(7) 0.0039(6) -0.0070(6) -0.0043(6) C24A 0.0451(10) 0.0478(10) 0.0279(8) 0.0054(7) -0.0041(7) -0.0117(8) C25A 0.0411(10) 0.0486(10) 0.0324(8) 0.0022(7) 0.0061(7) -0.0067(8) C26A 0.0334(8) 0.0381(9) 0.0353(8) 0.0035(7) -0.0012(6) -0.0010(7) O1B 0.0418(7) 0.0541(8) 0.0285(6) -0.0001(5) -0.0057(5) 0.0054(6) C1B 0.0306(7) 0.0345(8) 0.0237(7) -0.0012(6) 0.0002(5) -0.0057(6) N1B 0.0382(7) 0.0364(7) 0.0226(6) -0.0039(5) -0.0043(5) 0.0000(6) C11B 0.0280(7) 0.0385(8) 0.0267(7) -0.0079(6) -0.0009(6) -0.0066(6) C12B 0.0360(8) 0.0404(9) 0.0286(7) -0.0051(6) -0.0002(6) -0.0092(7) C13B 0.0324(8) 0.0581(11) 0.0290(8) -0.0088(7) 0.0018(6) -0.0162(8) C14B 0.0351(9) 0.0616(12) 0.0401(9) -0.0244(9) 0.0049(7) -0.0146(8) C15B 0.0375(9) 0.0422(10) 0.0543(11) -0.0206(8) -0.0019(8) -0.0070(8) C16B 0.0360(9) 0.0378(9) 0.0385(9) -0.0060(7) -0.0047(7) -0.0065(7) C17B 0.0610(14) 0.0835(17) 0.0294(9) -0.0030(9) 0.0030(9) -0.0226(12) C21B 0.0302(7) 0.0283(7) 0.0244(6) -0.0010(5) 0.0002(5) -0.0049(6) C22B 0.0294(8) 0.0373(8) 0.0294(7) -0.0026(6) -0.0010(6) -0.0028(6) N23B 0.0364(7) 0.0396(8) 0.0326(7) -0.0087(6) 0.0023(6) -0.0037(6) C24B 0.0435(9) 0.0432(9) 0.0286(8) -0.0081(7) -0.0001(7) -0.0124(8) C25B 0.0361(9) 0.0494(10) 0.0335(8) -0.0061(7) -0.0069(7) -0.0107(8) C26B 0.0297(8) 0.0407(9) 0.0325(8) -0.0052(7) -0.0004(6) -0.0048(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1A C1A 1.217(2) . ? C1A N1A 1.354(2) . ? C1A C21A 1.502(2) . ? N1A C11A 1.417(2) . ? N1A H1A 0.91(2) . ? C11A C16A 1.391(2) . ? C11A C12A 1.391(2) . ? C12A C13A 1.398(2) . ? C12A H12A 0.9300 . ? C13A C14A 1.385(3) . ? C13A C17A 1.508(3) . ? C14A C15A 1.380(3) . ? C14A H14A 0.9300 . ? C15A C16A 1.383(3) . ? C15A H15A 0.9300 . ? C16A H16A 0.9300 . ? C17A H17A 0.9600 . ? C17A H17B 0.9600 . ? C17A H17C 0.9600 . ? C17A H17D 0.9600 . ? C17A H17E 0.9600 . ? C17A H17F 0.9600 . ? C21A C26A 1.382(2) . ? C21A C22A 1.392(2) . ? C22A N23A 1.338(2) . ? C22A H22A 0.9300 . ? N23A C24A 1.335(2) . ? C24A C25A 1.376(3) . ? C24A H24A 0.9300 . ? C25A C26A 1.381(2) . ? C25A H25A 0.9300 . ? C26A H26A 0.9300 . ? O1B C1B 1.2176(19) . ? C1B N1B 1.356(2) . ? C1B C21B 1.502(2) . ? N1B C11B 1.418(2) . ? N1B H1B 0.89(2) . ? C11B C16B 1.390(2) . ? C11B C12B 1.391(2) . ? C12B C13B 1.397(2) . ? C12B H12B 0.9300 . ? C13B C14B 1.385(3) . ? C13B C17B 1.510(3) . ? C14B C15B 1.385(3) . ? C14B H14B 0.9300 . ? C15B C16B 1.389(3) . ? C15B H15B 0.9300 . ? C16B H16B 0.9300 . ? C17B H17G 0.9600 . ? C17B H17H 0.9600 . ? C17B H17I 0.9600 . ? C17B H17J 0.9600 . ? C17B H17K 0.9600 . ? C17B H17L 0.9600 . ? C21B C26B 1.388(2) . ? C21B C22B 1.394(2) . ? C22B N23B 1.338(2) . ? C22B H22B 0.9300 . ? N23B C24B 1.335(2) . ? C24B C25B 1.379(3) . ? C24B H24B 0.9300 . ? C25B C26B 1.382(2) . ? C25B H25B 0.9300 . ? C26B H26B 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 O1A C1A N1A 124.68(15) . . ? O1A C1A C21A 120.84(15) . . ? N1A C1A C21A 114.48(14) . . ? C1A N1A C11A 127.54(14) . . ? C1A N1A H1A 118.5(15) . . ? C11A N1A H1A 113.8(15) . . ? C16A C11A C12A 119.71(15) . . ? C16A C11A N1A 117.06(15) . . ? C12A C11A N1A 123.13(15) . . ? C11A C12A C13A 120.20(17) . . ? C11A C12A H12A 119.9 . . ? C13A C12A H12A 119.9 . . ? C14A C13A C12A 119.53(17) . . ? C14A C13A C17A 120.76(17) . . ? C12A C13A C17A 119.72(19) . . ? C15A C14A C13A 119.94(16) . . ? C15A C14A H14A 120.0 . . ? C13A C14A H14A 120.0 . . ? C14A C15A C16A 121.02(18) . . ? C14A C15A H15A 119.5 . . ? C16A C15A H15A 119.5 . . ? C15A C16A C11A 119.57(17) . . ? C15A C16A H16A 120.2 . . ? C11A C16A H16A 120.2 . . ? C13A C17A H17A 109.5 . . ? C13A C17A H17B 109.5 . . ? H17A C17A H17B 109.5 . . ? C13A C17A H17C 109.5 . . ? H17A C17A H17C 109.5 . . ? H17B C17A H17C 109.5 . . ? C13A C17A H17D 109.5 . . ? H17A C17A H17D 141.1 . . ? H17B C17A H17D 56.3 . . ? H17C C17A H17D 56.3 . . ? C13A C17A H17E 109.5 . . ? H17A C17A H17E 56.3 . . ? H17B C17A H17E 141.1 . . ? H17C C17A H17E 56.3 . . ? H17D C17A H17E 109.5 . . ? C13A C17A H17F 109.5 . . ? H17A C17A H17F 56.3 . . ? H17B C17A H17F 56.3 . . ? H17C C17A H17F 141.1 . . ? H17D C17A H17F 109.5 . . ? H17E C17A H17F 109.5 . . ? C26A C21A C22A 118.15(15) . . ? C26A C21A C1A 123.46(14) . . ? C22A C21A C1A 118.38(14) . . ? N23A C22A C21A 123.39(16) . . ? N23A C22A H22A 118.3 . . ? C21A C22A H22A 118.3 . . ? C24A N23A C22A 117.08(15) . . ? N23A C24A C25A 123.68(16) . . ? N23A C24A H24A 118.2 . . ? C25A C24A H24A 118.2 . . ? C24A C25A C26A 118.73(17) . . ? C24A C25A H25A 120.6 . . ? C26A C25A H25A 120.6 . . ? C25A C26A C21A 118.96(16) . . ? C25A C26A H26A 120.5 . . ? C21A C26A H26A 120.5 . . ? O1B C1B N1B 124.49(15) . . ? O1B C1B C21B 120.63(14) . . ? N1B C1B C21B 114.88(13) . . ? C1B N1B C11B 125.74(14) . . ? C1B N1B H1B 118.4(14) . . ? C11B N1B H1B 115.2(14) . . ? C16B C11B C12B 120.03(15) . . ? C16B C11B N1B 117.45(15) . . ? C12B C11B N1B 122.42(15) . . ? C11B C12B C13B 120.37(17) . . ? C11B C12B H12B 119.8 . . ? C13B C12B H12B 119.8 . . ? C14B C13B C12B 119.23(17) . . ? C14B C13B C17B 120.81(17) . . ? C12B C13B C17B 119.95(19) . . ? C13B C14B C15B 120.32(16) . . ? C13B C14B H14B 119.8 . . ? C15B C14B H14B 119.8 . . ? C14B C15B C16B 120.68(18) . . ? C14B C15B H15B 119.7 . . ? C16B C15B H15B 119.7 . . ? C15B C16B C11B 119.35(18) . . ? C15B C16B H16B 120.3 . . ? C11B C16B H16B 120.3 . . ? C13B C17B H17G 109.5 . . ? C13B C17B H17H 109.5 . . ? H17G C17B H17H 109.5 . . ? C13B C17B H17I 109.5 . . ? H17G C17B H17I 109.5 . . ? H17H C17B H17I 109.5 . . ? C13B C17B H17J 109.5 . . ? H17G C17B H17J 141.1 . . ? H17H C17B H17J 56.3 . . ? H17I C17B H17J 56.3 . . ? C13B C17B H17K 109.5 . . ? H17G C17B H17K 56.3 . . ? H17H C17B H17K 141.1 . . ? H17I C17B H17K 56.3 . . ? H17J C17B H17K 109.5 . . ? C13B C17B H17L 109.5 . . ? H17G C17B H17L 56.3 . . ? H17H C17B H17L 56.3 . . ? H17I C17B H17L 141.1 . . ? H17J C17B H17L 109.5 . . ? H17K C17B H17L 109.5 . . ? C26B C21B C22B 118.15(14) . . ? C26B C21B C1B 124.34(14) . . ? C22B C21B C1B 117.46(14) . . ? N23B C22B C21B 123.31(15) . . ? N23B C22B H22B 118.3 . . ? C21B C22B H22B 118.3 . . ? C24B N23B C22B 117.37(15) . . ? N23B C24B C25B 123.48(15) . . ? N23B C24B H24B 118.3 . . ? C25B C24B H24B 118.3 . . ? C24B C25B C26B 118.88(16) . . ? C24B C25B H25B 120.6 . . ? C26B C25B H25B 120.6 . . ? C25B C26B C21B 118.79(15) . . ? C25B C26B H26B 120.6 . . ? C21B C26B H26B 120.6 . . ? 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 O1A C1A N1A C11A -0.9(3) . . . . ? C21A C1A N1A C11A 178.88(16) . . . . ? C1A N1A C11A C16A 158.33(18) . . . . ? C1A N1A C11A C12A -25.4(3) . . . . ? C16A C11A C12A C13A 2.1(3) . . . . ? N1A C11A C12A C13A -174.09(16) . . . . ? C11A C12A C13A C14A -1.1(3) . . . . ? C11A C12A C13A C17A 178.33(18) . . . . ? C12A C13A C14A C15A -0.5(3) . . . . ? C17A C13A C14A C15A 179.99(19) . . . . ? C13A C14A C15A C16A 1.3(3) . . . . ? C14A C15A C16A C11A -0.4(3) . . . . ? C12A C11A C16A C15A -1.3(3) . . . . ? N1A C11A C16A C15A 175.07(17) . . . . ? O1A C1A C21A C26A 145.1(2) . . . . ? N1A C1A C21A C26A -34.7(3) . . . . ? O1A C1A C21A C22A -33.5(3) . . . . ? N1A C1A C21A C22A 146.67(17) . . . . ? C26A C21A C22A N23A 1.1(3) . . . . ? C1A C21A C22A N23A 179.76(17) . . . . ? C21A C22A N23A C24A -0.4(3) . . . . ? C22A N23A C24A C25A -0.7(3) . . . . ? N23A C24A C25A C26A 0.9(3) . . . . ? C24A C25A C26A C21A -0.1(3) . . . . ? C22A C21A C26A C25A -0.8(3) . . . . ? C1A C21A C26A C25A -179.43(18) . . . . ? O1B C1B N1B C11B -2.1(3) . . . . ? C21B C1B N1B C11B 177.17(16) . . . . ? C1B N1B C11B C16B 147.23(18) . . . . ? C1B N1B C11B C12B -36.5(3) . . . . ? C16B C11B C12B C13B 1.5(3) . . . . ? N1B C11B C12B C13B -174.73(16) . . . . ? C11B C12B C13B C14B -1.2(3) . . . . ? C11B C12B C13B C17B 177.68(18) . . . . ? C12B C13B C14B C15B 0.3(3) . . . . ? C17B C13B C14B C15B -178.62(19) . . . . ? C13B C14B C15B C16B 0.5(3) . . . . ? C14B C15B C16B C11B -0.2(3) . . . . ? C12B C11B C16B C15B -0.7(3) . . . . ? N1B C11B C16B C15B 175.64(16) . . . . ? O1B C1B C21B C26B 149.71(18) . . . . ? N1B C1B C21B C26B -29.6(2) . . . . ? O1B C1B C21B C22B -27.8(2) . . . . ? N1B C1B C21B C22B 152.85(16) . . . . ? C26B C21B C22B N23B 0.7(3) . . . . ? C1B C21B C22B N23B 178.42(16) . . . . ? C21B C22B N23B C24B -0.3(3) . . . . ? C22B N23B C24B C25B -0.6(3) . . . . ? N23B C24B C25B C26B 1.0(3) . . . . ? C24B C25B C26B C21B -0.5(3) . . . . ? C22B C21B C26B C25B -0.3(3) . . . . ? C1B C21B C26B C25B -177.85(16) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # # Hydrogen bonding scheme # ======== ======= ====== # # D H A D-H H...A D...A D-H...A symm publ # - - - --- ----- ----- ------- ---- ---- N1A H1A N23B 0.91(2) 2.23(2) 3.090(2) 157(2) 2_655 yes N1B H1B N23A 0.89(2) 2.22(2) 3.078(2) 160.7(19) 2_565 yes C12A H12A O1A 0.93 2.38 2.929(2) 117 . yes C12B H12B O1B 0.93 2.49 2.952(2) 111 . yes C14A H14A O1B 0.93 2.50 3.343(2) 151 2_656 yes C14B H14B O1A 0.93 2.50 3.328(2) 148 2_566 yes C22A H22A Cg1 0.93 2.82 3.555(2) 137 2_555 yes C22B H22B Cg2 0.93 2.76 3.512(2) 138 2_666 yes # Cg1 and Cg2 are the C~6~ aromatic ring centroids located # at sites 2_555 as [-X,-Y,-Z] and 2_666 as [1-X,1-Y,1-Z]. # # Two extra C-H...Pi interactions are for C15A-H15A 1_545 and # C15B-H15B at 1_566 and involve the pyridinyl heteroaromatic rings. # Complete details for the C-H...\p(arene) interaction # C15B H15B C21A 0.93 3.00 3.691(2) 132 1_566 yes # C22A H22A C11A 0.93 3.20 3.956(2) 140.3 2 # C22A H22A C12A 0.93 3.26 3.799(3) 118.9 2 # C22A H22A C13A 0.93 3.23 3.677(3) 111.7 2 # C22A H22A C14A 0.93 3.10 3.691(3) 122.7 2 # C22A H22A C15A 0.93 3.00 3.812(3) 147.4 2 # C22A H22A C16A 0.93 3.05 3.951(3) 163.3 2 # C22B H22B C11B 0.93 3.04 3.842(2) 145.9 2_666 # C22B H22B C12B 0.93 3.23 3.816(3) 123.1 2_666 # C22B H22B C13B 0.93 3.30 3.771(3) 113.6 2_666 # C22B H22B C14B 0.93 3.15 3.718(3) 120.8 2_666 # C22B H22B C15B 0.93 2.94 3.722(3) 143.0 2_666 # C22B H22B C16B 0.93 2.88 3.791(2) 166.7 2_666 #============================================================ data_NmoM_[10-007] _database_code_depnum_ccdc_archive 'CCDC 809623' #TrackingRef 'NxxM_5-Cl-NoxM_fin.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common NmoM _chemical_melting_point 380 _chemical_formula_moiety 'C13 H12 N2 O' _chemical_formula_sum 'C13 H12 N2 O' _chemical_formula_weight 212.25 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab' 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' '-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 8.0664(2) _cell_length_b 9.4009(2) _cell_length_c 29.5324(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2239.48(10) _cell_formula_units_Z 8 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 3736 _cell_measurement_theta_min 3.4 _cell_measurement_theta_max 27.0 _exptl_crystal_description Plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.259 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 896 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_T_min 0.967 _exptl_absorpt_correction_type Analytical _exptl_absorpt_process_details '(ABSFAC, Clark and Reid, 1998)' _exptl_absorpt_correction_T_max 0.995 _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Xcalibur, Sapphire3, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_standards_number 14454 _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 1 _diffrn_reflns_number 13292 _diffrn_reflns_av_R_equivalents 0.0360 _diffrn_reflns_av_sigmaI/netI 0.0282 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -37 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 3.40 _diffrn_reflns_theta_max 27.09 _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 27.09 _diffrn_measured_fraction_theta_full 0.999 _reflns_number_total 2421 _reflns_number_gt 1591 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008) and SORTX (McArdle, 1995)' _computing_molecular_graphics 'PLATON (Spek, 2009)' _computing_publication_material SHELXL97 _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 'w=1/[\s^2^(Fo^2^)+(0.0598P)^2^] 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 2421 _refine_ls_number_parameters 150 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0660 _refine_ls_R_factor_gt 0.0396 _refine_ls_wR_factor_ref 0.1070 _refine_ls_wR_factor_gt 0.1002 _refine_ls_goodness_of_fit_ref 0.977 _refine_ls_restrained_S_all 0.977 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.152 _refine_diff_density_min -0.135 _refine_diff_density_rms 0.028 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.15421(13) 0.13342(9) 0.15084(4) 0.0566(3) Uani 1 1 d . . . N1 N 0.25875(15) -0.07726(13) 0.12674(4) 0.0448(3) Uani 1 1 d . . . H1 H 0.2702(19) -0.1639(18) 0.1350(6) 0.059(5) Uiso 1 1 d . . . C1 C 0.15278(16) 0.00319(13) 0.15133(5) 0.0409(3) Uani 1 1 d . . . C11 C 0.39073(17) -0.01761(13) 0.10086(5) 0.0424(3) Uani 1 1 d . . . C12 C 0.35697(18) 0.07063(15) 0.06418(5) 0.0503(4) Uani 1 1 d . . . C13 C 0.4926(2) 0.12973(19) 0.04200(6) 0.0664(5) Uani 1 1 d . . . H13 H 0.4741 0.1913 0.0179 0.080 Uiso 1 1 calc R . . C14 C 0.6524(2) 0.1004(2) 0.05444(6) 0.0717(5) Uani 1 1 d . . . H14 H 0.7402 0.1431 0.0392 0.086 Uiso 1 1 calc R . . C15 C 0.6829(2) 0.00797(18) 0.08934(6) 0.0669(5) Uani 1 1 d . . . H15 H 0.7912 -0.0147 0.0973 0.080 Uiso 1 1 calc R . . C16 C 0.55175(18) -0.05113(16) 0.11257(5) 0.0547(4) Uani 1 1 d . . . H16 H 0.5718 -0.1140 0.1363 0.066 Uiso 1 1 calc R . . C17 C 0.1837(2) 0.09893(19) 0.04772(6) 0.0696(5) Uani 1 1 d . . . H17A H 0.1868 0.1248 0.0163 0.104 Uiso 1 1 calc R . . H17B H 0.1360 0.1753 0.0649 0.104 Uiso 1 1 calc R . . H17C H 0.1176 0.0148 0.0514 0.104 Uiso 1 1 calc R . . C21 C 0.02972(15) -0.07597(13) 0.17910(4) 0.0382(3) Uani 1 1 d . . . C22 C -0.02989(17) -0.01291(15) 0.21814(5) 0.0493(4) Uani 1 1 d . . . H22 H 0.0092 0.0773 0.2254 0.059 Uiso 1 1 calc R . . N23 N -0.13950(16) -0.07233(13) 0.24612(5) 0.0578(4) Uani 1 1 d . . . C24 C -0.19473(19) -0.20064(16) 0.23447(6) 0.0579(4) Uani 1 1 d . . . H24 H -0.2717 -0.2447 0.2533 0.069 Uiso 1 1 calc R . . C25 C -0.14451(19) -0.27114(15) 0.19640(5) 0.0579(4) Uani 1 1 d . . . H25 H -0.1874 -0.3605 0.1897 0.069 Uiso 1 1 calc R . . C26 C -0.03001(18) -0.20896(15) 0.16813(5) 0.0492(4) Uani 1 1 d . . . H26 H 0.0063 -0.2556 0.1422 0.059 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 O1 0.0660(7) 0.0266(5) 0.0770(8) 0.0045(5) 0.0122(6) -0.0002(4) N1 0.0498(7) 0.0267(6) 0.0578(7) 0.0076(5) 0.0082(6) 0.0022(5) C1 0.0428(7) 0.0286(7) 0.0514(8) 0.0053(6) -0.0028(6) 0.0009(5) C11 0.0472(8) 0.0303(7) 0.0497(8) 0.0003(6) 0.0049(6) -0.0003(6) C12 0.0546(9) 0.0451(8) 0.0512(9) 0.0056(7) 0.0005(7) -0.0005(7) C13 0.0722(12) 0.0653(11) 0.0618(11) 0.0184(8) 0.0104(9) -0.0060(9) C14 0.0598(11) 0.0766(12) 0.0786(13) 0.0081(10) 0.0192(10) -0.0116(9) C15 0.0463(9) 0.0741(12) 0.0804(12) -0.0013(10) 0.0051(8) 0.0010(8) C16 0.0529(9) 0.0486(9) 0.0625(10) 0.0047(7) 0.0020(8) 0.0060(7) C17 0.0669(11) 0.0784(12) 0.0634(11) 0.0163(9) -0.0077(9) 0.0073(9) C21 0.0368(7) 0.0293(6) 0.0484(8) 0.0041(6) -0.0030(6) 0.0043(5) C22 0.0441(8) 0.0383(8) 0.0654(10) -0.0063(7) 0.0023(7) 0.0021(6) N23 0.0543(8) 0.0544(8) 0.0646(8) -0.0060(6) 0.0134(7) 0.0025(6) C24 0.0545(9) 0.0501(9) 0.0690(11) 0.0067(8) 0.0165(8) -0.0011(7) C25 0.0630(9) 0.0398(8) 0.0709(10) -0.0024(7) 0.0150(8) -0.0120(7) C26 0.0562(9) 0.0372(8) 0.0542(8) -0.0019(6) 0.0087(7) -0.0046(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 O1 C1 1.2244(15) . ? N1 C1 1.3529(17) . ? N1 C11 1.4255(17) . ? N1 H1 0.855(17) . ? C1 C21 1.4872(18) . ? C11 C16 1.3805(19) . ? C11 C12 1.3913(19) . ? C12 C13 1.391(2) . ? C12 C17 1.504(2) . ? C13 C14 1.368(3) . ? C13 H13 0.9300 . ? C14 C15 1.370(2) . ? C14 H14 0.9300 . ? C15 C16 1.378(2) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C21 C26 1.3786(19) . ? C21 C22 1.3827(19) . ? C22 N23 1.3329(19) . ? C22 H22 0.9300 . ? N23 C24 1.3310(19) . ? C24 C25 1.366(2) . ? C24 H24 0.9300 . ? C25 C26 1.3755(19) . ? C25 H25 0.9300 . ? C26 H26 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 C1 N1 C11 122.67(11) . . ? C1 N1 H1 116.6(11) . . ? C11 N1 H1 116.5(11) . . ? O1 C1 N1 123.14(12) . . ? O1 C1 C21 120.88(12) . . ? N1 C1 C21 115.98(11) . . ? C16 C11 C12 121.02(13) . . ? C16 C11 N1 118.59(12) . . ? C12 C11 N1 120.38(12) . . ? C13 C12 C11 116.80(14) . . ? C13 C12 C17 120.55(14) . . ? C11 C12 C17 122.63(13) . . ? C14 C13 C12 122.26(16) . . ? C14 C13 H13 118.9 . . ? C12 C13 H13 118.9 . . ? C13 C14 C15 119.93(16) . . ? C13 C14 H14 120.0 . . ? C15 C14 H14 120.0 . . ? C14 C15 C16 119.50(16) . . ? C14 C15 H15 120.2 . . ? C16 C15 H15 120.2 . . ? C15 C16 C11 120.37(15) . . ? C15 C16 H16 119.8 . . ? C11 C16 H16 119.8 . . ? C12 C17 H17A 109.5 . . ? C12 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C12 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C26 C21 C22 117.60(13) . . ? C26 C21 C1 123.88(12) . . ? C22 C21 C1 118.52(12) . . ? N23 C22 C21 124.60(13) . . ? N23 C22 H22 117.7 . . ? C21 C22 H22 117.7 . . ? C24 N23 C22 116.20(13) . . ? N23 C24 C25 123.58(14) . . ? N23 C24 H24 118.2 . . ? C25 C24 H24 118.2 . . ? C24 C25 C26 119.50(14) . . ? C24 C25 H25 120.3 . . ? C26 C25 H25 120.3 . . ? C25 C26 C21 118.51(13) . . ? C25 C26 H26 120.7 . . ? C21 C26 H26 120.7 . . ? 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 C1 O1 5.3(2) . . . . ? C11 N1 C1 C21 -175.65(12) . . . . ? C1 N1 C11 C16 116.45(15) . . . . ? C1 N1 C11 C12 -64.55(18) . . . . ? C16 C11 C12 C13 -3.9(2) . . . . ? N1 C11 C12 C13 177.12(13) . . . . ? C16 C11 C12 C17 174.24(15) . . . . ? N1 C11 C12 C17 -4.7(2) . . . . ? C11 C12 C13 C14 1.8(3) . . . . ? C17 C12 C13 C14 -176.41(17) . . . . ? C12 C13 C14 C15 1.2(3) . . . . ? C13 C14 C15 C16 -2.1(3) . . . . ? C14 C15 C16 C11 0.0(2) . . . . ? C12 C11 C16 C15 3.1(2) . . . . ? N1 C11 C16 C15 -177.89(14) . . . . ? O1 C1 C21 C26 150.67(14) . . . . ? N1 C1 C21 C26 -28.38(19) . . . . ? O1 C1 C21 C22 -28.87(19) . . . . ? N1 C1 C21 C22 152.09(12) . . . . ? C26 C21 C22 N23 0.8(2) . . . . ? C1 C21 C22 N23 -179.64(13) . . . . ? C21 C22 N23 C24 -0.9(2) . . . . ? C22 N23 C24 C25 0.3(2) . . . . ? N23 C24 C25 C26 0.4(3) . . . . ? C24 C25 C26 C21 -0.5(2) . . . . ? C22 C21 C26 C25 -0.1(2) . . . . ? C1 C21 C26 C25 -179.62(13) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # # Hydrogen bonding scheme # ======== ======= ====== # # D H A D-H H...A D...A D-H...A symm publ # - - - --- ----- ----- ------- ---- ---- N1 H1 O1 0.855(17) 2.055(18) 2.8978(15) 168.6(15) 8_655 yes C17 H17B O1 0.96 2.57 3.072(2) 113 . yes C26 H26 Cg1 0.93 2.72 3.5751(16) 152 7_545 yes # C26 H26 C11 0.93 2.87 3.6916(19) 147.7 8_655 # C26 H26 C12 0.93 3.03 3.958(2) 174.0 8_655 # C26 H26 C13 0.93 3.15 4.033(2) 159.4 8_655 # C26 H26 C14 0.93 3.19 3.932(2) 138.0 8_655 # C26 H26 C15 0.93 3.12 3.744(2) 126.5 8_655 # C26 H26 C16 0.93 2.95 3.615(2) 129.7 8_655 # Cg1 is the C~6~ aromatic ring centroid located # at sites 7_545 = [1/2-X,-1/2+Y,Z] # Complete details for the C-H...\p(arene) interaction #============================================================ data_NopM_[10-008] _database_code_depnum_ccdc_archive 'CCDC 809624' #TrackingRef 'NxxM_5-Cl-NoxM_fin.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common NopM _chemical_melting_point 378 _chemical_formula_moiety 'C13 H12 N2 O' _chemical_formula_sum 'C13 H12 N2 O' _chemical_formula_weight 212.25 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 Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 6.0828(2) _cell_length_b 27.0507(8) _cell_length_c 7.1963(3) _cell_angle_alpha 90.00 _cell_angle_beta 111.673(4) _cell_angle_gamma 90.00 _cell_volume 1100.40(7) _cell_formula_units_Z 4 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 1684 _cell_measurement_theta_min 3.6 _cell_measurement_theta_max 25.4 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.281 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_T_min 0.980 _exptl_absorpt_correction_type Analytical _exptl_absorpt_process_details '(ABSFAC, Clark and Reid, 1998)' _exptl_absorpt_correction_T_max 0.995 _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Xcalibur, Sapphire3, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_standards_number 6149 _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 1 _diffrn_reflns_number 6058 _diffrn_reflns_av_R_equivalents 0.0375 _diffrn_reflns_av_sigmaI/netI 0.0358 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -32 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 3.60 _diffrn_reflns_theta_max 25.44 _diffrn_measured_fraction_theta_max 0.966 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _reflns_number_total 1970 _reflns_number_gt 1176 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008) and SORTX (McArdle, 1995)' _computing_molecular_graphics 'PLATON (Spek, 2009)' _computing_publication_material SHELXL97 _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 'w=1/[\s^2^(Fo^2^)+(0.0418P)^2^] 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 1970 _refine_ls_number_parameters 150 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0664 _refine_ls_R_factor_gt 0.0347 _refine_ls_wR_factor_ref 0.0828 _refine_ls_wR_factor_gt 0.0759 _refine_ls_goodness_of_fit_ref 0.842 _refine_ls_restrained_S_all 0.842 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.139 _refine_diff_density_min -0.106 _refine_diff_density_rms 0.025 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O -0.20062(17) 0.33392(4) 0.15165(18) 0.0777(4) Uani 1 1 d . . . N1 N 0.1972(2) 0.34173(5) 0.23829(18) 0.0565(3) Uani 1 1 d . . . H1 H 0.325(3) 0.3223(6) 0.260(2) 0.064(5) Uiso 1 1 d . . . C1 C -0.0041(3) 0.31549(6) 0.1947(2) 0.0542(4) Uani 1 1 d . . . C11 C 0.2219(2) 0.39373(5) 0.2388(2) 0.0509(4) Uani 1 1 d . . . C12 C 0.0732(2) 0.42553(6) 0.2867(2) 0.0611(4) Uani 1 1 d . . . H12 H -0.0513 0.4131 0.3182 0.073 Uiso 1 1 calc R . . C13 C 0.1104(3) 0.47583(6) 0.2876(2) 0.0645(4) Uani 1 1 d . . . H13 H 0.0084 0.4969 0.3193 0.077 Uiso 1 1 calc R . . C14 C 0.2929(3) 0.49610(6) 0.2431(2) 0.0581(4) Uani 1 1 d . . . C15 C 0.4396(3) 0.46357(6) 0.1977(2) 0.0630(4) Uani 1 1 d . . . H15 H 0.5656 0.4760 0.1683 0.076 Uiso 1 1 calc R . . C16 C 0.4059(3) 0.41321(6) 0.1942(2) 0.0604(4) Uani 1 1 d . . . H16 H 0.5076 0.3923 0.1617 0.072 Uiso 1 1 calc R . . C17 C 0.3298(3) 0.55122(6) 0.2462(3) 0.0778(5) Uani 1 1 d . . . H17A H 0.4754 0.5582 0.2284 0.117 Uiso 0.60 1 calc PR . . H17B H 0.3366 0.5643 0.3723 0.117 Uiso 0.60 1 calc PR . . H17C H 0.2008 0.5662 0.1401 0.117 Uiso 0.60 1 calc PR . . H17D H 0.1998 0.5676 0.2654 0.117 Uiso 0.40 1 calc PR . . H17E H 0.3386 0.5616 0.1216 0.117 Uiso 0.40 1 calc PR . . H17F H 0.4744 0.5596 0.3538 0.117 Uiso 0.40 1 calc PR . . C21 C 0.0292(2) 0.26071(5) 0.2019(2) 0.0499(4) Uani 1 1 d . . . N22 N 0.2510(2) 0.24425(5) 0.26109(18) 0.0595(4) Uani 1 1 d . . . C23 C 0.2803(3) 0.19540(6) 0.2696(3) 0.0694(5) Uani 1 1 d . . . H23 H 0.4339 0.1831 0.3126 0.083 Uiso 1 1 calc R . . C24 C 0.0976(3) 0.16210(6) 0.2189(2) 0.0690(5) Uani 1 1 d . . . H24 H 0.1271 0.1283 0.2269 0.083 Uiso 1 1 calc R . . C25 C -0.1282(3) 0.17962(6) 0.1565(3) 0.0725(5) Uani 1 1 d . . . H25 H -0.2559 0.1580 0.1196 0.087 Uiso 1 1 calc R . . C26 C -0.1640(3) 0.22998(6) 0.1489(2) 0.0643(4) Uani 1 1 d . . . H26 H -0.3161 0.2429 0.1088 0.077 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 O1 0.0503(6) 0.0637(7) 0.1105(9) -0.0088(6) 0.0197(6) 0.0067(5) N1 0.0485(7) 0.0509(8) 0.0673(9) -0.0020(6) 0.0182(6) 0.0052(6) C1 0.0487(9) 0.0583(10) 0.0524(9) -0.0030(7) 0.0149(7) 0.0043(8) C11 0.0477(8) 0.0483(9) 0.0521(9) -0.0038(7) 0.0131(7) 0.0044(7) C12 0.0545(9) 0.0626(11) 0.0689(10) -0.0098(8) 0.0259(8) 0.0011(8) C13 0.0602(10) 0.0587(11) 0.0717(11) -0.0121(8) 0.0209(8) 0.0095(8) C14 0.0578(9) 0.0541(10) 0.0529(9) -0.0028(7) 0.0094(7) 0.0032(8) C15 0.0566(9) 0.0584(11) 0.0757(11) 0.0011(8) 0.0264(8) 0.0001(8) C16 0.0513(9) 0.0570(10) 0.0752(11) -0.0035(8) 0.0260(8) 0.0061(7) C17 0.0936(12) 0.0550(10) 0.0765(12) -0.0020(8) 0.0216(10) 0.0017(9) C21 0.0491(9) 0.0540(9) 0.0445(8) 0.0003(7) 0.0147(6) 0.0026(7) N22 0.0559(8) 0.0555(9) 0.0655(9) 0.0049(6) 0.0207(6) 0.0067(6) C23 0.0653(11) 0.0615(12) 0.0810(12) 0.0086(8) 0.0266(9) 0.0135(8) C24 0.0819(12) 0.0491(10) 0.0762(12) 0.0047(8) 0.0295(9) 0.0056(9) C25 0.0709(11) 0.0573(11) 0.0856(13) -0.0010(9) 0.0244(9) -0.0067(9) C26 0.0548(9) 0.0611(11) 0.0729(11) -0.0006(8) 0.0189(8) 0.0008(8) _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 C1 1.2246(15) . ? N1 C1 1.3482(18) . ? N1 C11 1.4145(18) . ? N1 H1 0.903(15) . ? C1 C21 1.494(2) . ? C11 C16 1.3783(19) . ? C11 C12 1.3808(19) . ? C12 C13 1.379(2) . ? C12 H12 0.9300 . ? C13 C14 1.378(2) . ? C13 H13 0.9300 . ? C14 C15 1.376(2) . ? C14 C17 1.507(2) . ? C15 C16 1.376(2) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C17 H17D 0.9600 . ? C17 H17E 0.9600 . ? C17 H17F 0.9600 . ? C21 N22 1.3325(16) . ? C21 C26 1.3732(19) . ? N22 C23 1.3317(19) . ? C23 C24 1.371(2) . ? C23 H23 0.9300 . ? C24 C25 1.363(2) . ? C24 H24 0.9300 . ? C25 C26 1.378(2) . ? C25 H25 0.9300 . ? C26 H26 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 C1 N1 C11 127.62(13) . . ? C1 N1 H1 112.7(9) . . ? C11 N1 H1 119.6(9) . . ? O1 C1 N1 124.22(14) . . ? O1 C1 C21 121.31(14) . . ? N1 C1 C21 114.47(13) . . ? C16 C11 C12 118.89(14) . . ? C16 C11 N1 118.30(13) . . ? C12 C11 N1 122.80(14) . . ? C13 C12 C11 119.64(15) . . ? C13 C12 H12 120.2 . . ? C11 C12 H12 120.2 . . ? C14 C13 C12 122.44(14) . . ? C14 C13 H13 118.8 . . ? C12 C13 H13 118.8 . . ? C15 C14 C13 116.72(14) . . ? C15 C14 C17 122.05(15) . . ? C13 C14 C17 121.23(14) . . ? C14 C15 C16 122.14(15) . . ? C14 C15 H15 118.9 . . ? C16 C15 H15 118.9 . . ? C15 C16 C11 120.17(14) . . ? C15 C16 H16 119.9 . . ? C11 C16 H16 119.9 . . ? C14 C17 H17A 109.5 . . ? C14 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C14 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C14 C17 H17D 109.5 . . ? H17A C17 H17D 141.1 . . ? H17B C17 H17D 56.3 . . ? H17C C17 H17D 56.3 . . ? C14 C17 H17E 109.5 . . ? H17A C17 H17E 56.3 . . ? H17B C17 H17E 141.1 . . ? H17C C17 H17E 56.3 . . ? H17D C17 H17E 109.5 . . ? C14 C17 H17F 109.5 . . ? H17A C17 H17F 56.3 . . ? H17B C17 H17F 56.3 . . ? H17C C17 H17F 141.1 . . ? H17D C17 H17F 109.5 . . ? H17E C17 H17F 109.5 . . ? N22 C21 C26 123.23(14) . . ? N22 C21 C1 116.80(13) . . ? C26 C21 C1 119.97(13) . . ? C23 N22 C21 116.67(13) . . ? N22 C23 C24 123.91(15) . . ? N22 C23 H23 118.0 . . ? C24 C23 H23 118.0 . . ? C25 C24 C23 118.59(15) . . ? C25 C24 H24 120.7 . . ? C23 C24 H24 120.7 . . ? C24 C25 C26 118.83(15) . . ? C24 C25 H25 120.6 . . ? C26 C25 H25 120.6 . . ? C21 C26 C25 118.75(14) . . ? C21 C26 H26 120.6 . . ? C25 C26 H26 120.6 . . ? 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 C1 O1 -1.6(2) . . . . ? C11 N1 C1 C21 178.22(13) . . . . ? C1 N1 C11 C16 -149.96(14) . . . . ? C1 N1 C11 C12 31.7(2) . . . . ? C16 C11 C12 C13 0.5(2) . . . . ? N1 C11 C12 C13 178.85(13) . . . . ? C11 C12 C13 C14 -0.4(2) . . . . ? C12 C13 C14 C15 -0.2(2) . . . . ? C12 C13 C14 C17 -179.70(14) . . . . ? C13 C14 C15 C16 0.7(2) . . . . ? C17 C14 C15 C16 -179.83(14) . . . . ? C14 C15 C16 C11 -0.6(2) . . . . ? C12 C11 C16 C15 0.0(2) . . . . ? N1 C11 C16 C15 -178.46(13) . . . . ? O1 C1 C21 N22 -176.34(13) . . . . ? N1 C1 C21 N22 3.87(18) . . . . ? O1 C1 C21 C26 3.6(2) . . . . ? N1 C1 C21 C26 -176.18(13) . . . . ? C26 C21 N22 C23 -0.7(2) . . . . ? C1 C21 N22 C23 179.22(13) . . . . ? C21 N22 C23 C24 1.0(2) . . . . ? N22 C23 C24 C25 -0.2(3) . . . . ? C23 C24 C25 C26 -0.7(2) . . . . ? N22 C21 C26 C25 -0.2(2) . . . . ? C1 C21 C26 C25 179.85(14) . . . . ? C24 C25 C26 C21 1.0(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # # Hydrogen bonding scheme # ======== ======= ====== # # D H A D-H H...A D...A D-H...A symm publ # - - - --- ----- ----- ------- ---- ---- N1 H1 N22 0.903(15) 2.160(15) 2.6548(18) 113.6(11) . yes C12 H12 O1 0.93 2.46 2.9436(18) 113 . yes C16 H16 O1 0.93 2.40 3.3111(18) 168 1_655 yes #============================================================ data_NomM_[10-009] _database_code_depnum_ccdc_archive 'CCDC 809625' #TrackingRef 'NxxM_5-Cl-NoxM_fin.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common NomM _chemical_melting_point 323 _chemical_formula_moiety 'C13 H12 N2 O' _chemical_formula_sum 'C13 H12 N2 O' _chemical_formula_weight 212.25 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 Monoclinic _symmetry_space_group_name_H-M 'P 21' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.2326(4) _cell_length_b 14.0836(4) _cell_length_c 9.4162(4) _cell_angle_alpha 90.00 _cell_angle_beta 105.661(4) _cell_angle_gamma 90.00 _cell_volume 1178.92(8) _cell_formula_units_Z 4 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 2146 _cell_measurement_theta_min 3.7 _cell_measurement_theta_max 27.8 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.196 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type Analytical _exptl_absorpt_correction_T_min 0.983 _exptl_absorpt_correction_T_max 0.996 _exptl_absorpt_process_details '(ABSFAC, Clark and Reid, 1998)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Xcalibur, Sapphire3, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_standards_number 15366 _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 1 _diffrn_reflns_number 16614 _diffrn_reflns_av_R_equivalents 0.0959 _diffrn_reflns_av_sigmaI/netI 0.1270 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.69 _diffrn_reflns_theta_max 27.96 _diffrn_measured_fraction_theta_max 0.942 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.995 _reflns_number_total 2780 _reflns_number_gt 1026 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008) and SORTX (McArdle, 1995)' _computing_molecular_graphics 'PLATON (Spek, 2009)' _computing_publication_material SHELXL97 _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 'w=1/[\s^2^(Fo^2^)+(0.0126P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0114(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ #_refine_ls_abs_structure_details 'Flack, 1983)' #_refine_ls_abs_structure_Flack 0.7(12) _refine_ls_number_reflns 2780 _refine_ls_number_parameters 298 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1375 _refine_ls_R_factor_gt 0.0292 _refine_ls_wR_factor_ref 0.0446 _refine_ls_wR_factor_gt 0.0362 _refine_ls_goodness_of_fit_ref 0.667 _refine_ls_restrained_S_all 0.667 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.075 _refine_diff_density_min -0.078 _refine_diff_density_rms 0.019 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 O1A O 0.3096(2) 0.34025(14) 0.14293(19) 0.0708(6) Uani 1 1 d . . . N1A N 0.2011(2) 0.41942(15) -0.0703(3) 0.0574(7) Uani 1 1 d . . . H1A H 0.143(3) 0.4736(17) -0.101(3) 0.069 Uiso 1 1 d . . . C1A C 0.2405(3) 0.4087(2) 0.0782(4) 0.0560(8) Uani 1 1 d . . . C11A C 0.2217(3) 0.3538(2) -0.1779(4) 0.0560(8) Uani 1 1 d . . . C12A C 0.3266(3) 0.2816(2) -0.1431(3) 0.0703(9) Uani 1 1 d . . . H12A H 0.3848 0.2733 -0.0466 0.084 Uiso 1 1 calc R . . C13A C 0.3440(4) 0.2207(2) -0.2561(5) 0.0796(10) Uani 1 1 d . . . C14A C 0.2597(4) 0.2341(2) -0.3956(4) 0.0839(11) Uani 1 1 d . . . H14A H 0.2710 0.1934 -0.4697 0.101 Uiso 1 1 calc R . . C15A C 0.1571(4) 0.3070(2) -0.4301(4) 0.0776(10) Uani 1 1 d . . . H15A H 0.1006 0.3161 -0.5270 0.093 Uiso 1 1 calc R . . C16A C 0.1382(3) 0.3666(2) -0.3204(4) 0.0648(9) Uani 1 1 d . . . H16A H 0.0684 0.4157 -0.3434 0.078 Uiso 1 1 calc R . . C17A C 0.4620(4) 0.1419(3) -0.2169(4) 0.1328(15) Uani 1 1 d . . . H17A H 0.4131 0.0823 -0.2118 0.199 Uiso 1 1 calc R . . H17B H 0.5315 0.1554 -0.1232 0.199 Uiso 1 1 calc R . . H17C H 0.5153 0.1384 -0.2913 0.199 Uiso 1 1 calc R . . C21A C 0.1885(3) 0.4871(2) 0.1608(4) 0.0537(8) Uani 1 1 d . . . N22A N 0.1063(3) 0.55616(18) 0.0816(2) 0.0736(8) Uani 1 1 d . . . C23A C 0.0573(4) 0.6224(2) 0.1584(4) 0.0909(11) Uani 1 1 d . . . H23A H 0.0016 0.6724 0.1064 0.109 Uiso 1 1 calc R . . C24A C 0.0832(4) 0.6219(3) 0.3074(5) 0.0954(12) Uani 1 1 d . . . H24A H 0.0426 0.6688 0.3547 0.114 Uiso 1 1 calc R . . C25A C 0.1692(4) 0.5517(3) 0.3857(4) 0.0928(11) Uani 1 1 d . . . H25A H 0.1911 0.5502 0.4881 0.111 Uiso 1 1 calc R . . C26A C 0.2235(3) 0.4826(2) 0.3099(4) 0.0753(10) Uani 1 1 d . . . H26A H 0.2833 0.4336 0.3605 0.090 Uiso 1 1 calc R . . O1B O -0.0517(2) 0.09052(14) 0.2918(2) 0.0785(6) Uani 1 1 d . . . N1B N 0.1384(3) 0.16432(16) 0.2211(3) 0.0587(7) Uani 1 1 d . . . H1B H 0.158(3) 0.2160(18) 0.179(3) 0.070 Uiso 1 1 d . . . C1B C -0.0018(4) 0.1580(2) 0.2370(3) 0.0585(8) Uani 1 1 d . . . C11B C 0.2541(3) 0.0949(2) 0.2545(3) 0.0549(8) Uani 1 1 d . . . C12B C 0.2443(3) 0.0138(2) 0.3309(3) 0.0745(10) Uani 1 1 d . . . H12B H 0.1590 0.0026 0.3630 0.089 Uiso 1 1 calc R . . C13B C 0.3601(4) -0.0522(2) 0.3612(3) 0.0781(10) Uani 1 1 d . . . C14B C 0.4864(4) -0.0352(2) 0.3161(3) 0.0793(10) Uani 1 1 d . . . H14B H 0.5646 -0.0791 0.3353 0.095 Uiso 1 1 calc R . . C15B C 0.4967(4) 0.0472(3) 0.2422(4) 0.0895(10) Uani 1 1 d . . . H15B H 0.5832 0.0593 0.2127 0.107 Uiso 1 1 calc R . . C16B C 0.3818(4) 0.1122(2) 0.2108(3) 0.0774(10) Uani 1 1 d . . . H16B H 0.3905 0.1678 0.1603 0.093 Uiso 1 1 calc R . . C17B C 0.3468(4) -0.1444(3) 0.4426(4) 0.1501(16) Uani 1 1 d . . . H17D H 0.3081 -0.1937 0.3722 0.225 Uiso 1 1 calc R . . H17E H 0.2797 -0.1349 0.5035 0.225 Uiso 1 1 calc R . . H17F H 0.4442 -0.1624 0.5033 0.225 Uiso 1 1 calc R . . C21B C -0.1001(3) 0.2427(2) 0.1813(3) 0.0582(8) Uani 1 1 d . . . N22B N -0.0572(3) 0.30126(19) 0.0896(3) 0.0733(8) Uani 1 1 d . . . C23B C -0.1489(5) 0.3735(3) 0.0367(4) 0.0963(12) Uani 1 1 d . . . H23B H -0.1223 0.4152 -0.0286 0.116 Uiso 1 1 calc R . . C24B C -0.2798(4) 0.3895(3) 0.0735(5) 0.1047(13) Uani 1 1 d . . . H24B H -0.3401 0.4412 0.0340 0.126 Uiso 1 1 calc R . . C25B C -0.3219(4) 0.3291(4) 0.1688(5) 0.1098(13) Uani 1 1 d . . . H25B H -0.4101 0.3393 0.1964 0.132 Uiso 1 1 calc R . . C26B C -0.2304(4) 0.2526(3) 0.2229(3) 0.0842(11) Uani 1 1 d . . . H26B H -0.2564 0.2089 0.2859 0.101 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 O1A 0.0786(14) 0.0676(15) 0.0704(15) 0.0125(12) 0.0275(11) 0.0237(13) N1A 0.0693(18) 0.0468(17) 0.062(2) 0.0040(16) 0.0283(15) 0.0125(13) C1A 0.061(2) 0.054(2) 0.059(2) 0.006(2) 0.0254(19) 0.0054(17) C11A 0.065(2) 0.046(2) 0.064(2) -0.0013(19) 0.0281(19) -0.0009(17) C12A 0.082(3) 0.063(2) 0.072(2) 0.000(2) 0.0298(18) 0.0089(19) C13A 0.102(3) 0.058(2) 0.091(3) -0.002(2) 0.047(3) 0.014(2) C14A 0.114(3) 0.060(2) 0.085(3) -0.023(2) 0.040(3) -0.006(2) C15A 0.093(3) 0.070(3) 0.065(2) -0.012(2) 0.0128(19) -0.013(2) C16A 0.072(2) 0.055(2) 0.067(2) -0.009(2) 0.018(2) -0.0007(17) C17A 0.180(4) 0.101(3) 0.138(3) 0.018(3) 0.078(3) 0.066(3) C21A 0.060(2) 0.050(2) 0.054(2) 0.0021(19) 0.0216(17) 0.0050(16) N22A 0.103(2) 0.0565(18) 0.067(2) 0.0013(17) 0.0329(15) 0.0203(16) C23A 0.137(3) 0.066(3) 0.078(3) 0.008(2) 0.043(2) 0.038(2) C24A 0.132(3) 0.075(3) 0.094(3) -0.004(3) 0.055(3) 0.026(2) C25A 0.129(3) 0.099(3) 0.056(3) -0.010(3) 0.034(2) 0.018(3) C26A 0.099(3) 0.071(2) 0.056(3) 0.007(2) 0.021(2) 0.019(2) O1B 0.0774(15) 0.0695(15) 0.0969(17) 0.0118(13) 0.0378(12) -0.0028(12) N1B 0.0648(18) 0.0432(16) 0.0702(18) 0.0036(13) 0.0218(15) -0.0022(16) C1B 0.059(2) 0.053(2) 0.062(2) -0.0091(18) 0.0148(18) -0.004(2) C11B 0.058(2) 0.044(2) 0.061(2) -0.0014(17) 0.0126(17) 0.0073(18) C12B 0.072(2) 0.063(2) 0.094(3) 0.015(2) 0.0320(19) 0.007(2) C13B 0.080(3) 0.066(2) 0.089(3) 0.015(2) 0.022(2) 0.007(2) C14B 0.084(3) 0.064(2) 0.094(3) 0.004(2) 0.030(2) 0.017(2) C15B 0.082(2) 0.081(3) 0.117(3) 0.016(2) 0.046(2) 0.021(2) C16B 0.081(3) 0.058(2) 0.103(3) 0.015(2) 0.043(2) 0.013(2) C17B 0.128(3) 0.104(3) 0.227(5) 0.093(3) 0.063(3) 0.030(3) C21B 0.056(2) 0.053(2) 0.062(2) -0.0046(18) 0.0081(18) -0.0004(19) N22B 0.0651(19) 0.0601(19) 0.088(2) 0.0130(16) 0.0088(15) 0.0048(16) C23B 0.080(3) 0.082(3) 0.122(3) 0.025(2) 0.018(2) 0.012(2) C24B 0.068(3) 0.103(3) 0.131(4) 0.002(3) 0.005(3) 0.028(3) C25B 0.079(3) 0.128(4) 0.124(3) 0.008(3) 0.031(2) 0.031(3) C26B 0.061(2) 0.093(3) 0.102(3) 0.012(2) 0.028(2) 0.015(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 O1A C1A 1.224(3) . ? N1A C1A 1.355(3) . ? N1A C11A 1.422(3) . ? N1A H1A 0.93(2) . ? C1A C21A 1.501(3) . ? C11A C16A 1.368(3) . ? C11A C12A 1.381(3) . ? C12A C13A 1.409(4) . ? C12A H12A 0.9300 . ? C13A C14A 1.348(4) . ? C13A C17A 1.529(4) . ? C14A C15A 1.375(4) . ? C14A H14A 0.9300 . ? C15A C16A 1.378(3) . ? C15A H15A 0.9300 . ? C16A H16A 0.9300 . ? C17A H17A 0.9600 . ? C17A H17B 0.9600 . ? C17A H17C 0.9600 . ? C21A N22A 1.332(3) . ? C21A C26A 1.355(3) . ? N22A C23A 1.332(3) . ? C23A C24A 1.359(3) . ? C23A H23A 0.9300 . ? C24A C25A 1.355(4) . ? C24A H24A 0.9300 . ? C25A C26A 1.379(4) . ? C25A H25A 0.9300 . ? C26A H26A 0.9300 . ? O1B C1B 1.229(3) . ? N1B C1B 1.345(3) . ? N1B C11B 1.420(3) . ? N1B H1B 0.87(2) . ? C1B C21B 1.505(4) . ? C11B C12B 1.367(3) . ? C11B C16B 1.371(3) . ? C12B C13B 1.386(4) . ? C12B H12B 0.9300 . ? C13B C14B 1.366(4) . ? C13B C17B 1.530(4) . ? C14B C15B 1.369(4) . ? C14B H14B 0.9300 . ? C15B C16B 1.372(3) . ? C15B H15B 0.9300 . ? C16B H16B 0.9300 . ? C17B H17D 0.9600 . ? C17B H17E 0.9600 . ? C17B H17F 0.9600 . ? C21B N22B 1.330(3) . ? C21B C26B 1.369(3) . ? N22B C23B 1.332(3) . ? C23B C24B 1.363(4) . ? C23B H23B 0.9300 . ? C24B C25B 1.367(4) . ? C24B H24B 0.9300 . ? C25B C26B 1.380(4) . ? C25B H25B 0.9300 . ? C26B H26B 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 C1A N1A C11A 127.8(3) . . ? C1A N1A H1A 112.6(15) . . ? C11A N1A H1A 119.1(15) . . ? O1A C1A N1A 124.1(3) . . ? O1A C1A C21A 121.2(3) . . ? N1A C1A C21A 114.7(3) . . ? C16A C11A C12A 120.2(3) . . ? C16A C11A N1A 117.7(3) . . ? C12A C11A N1A 122.0(3) . . ? C11A C12A C13A 119.0(3) . . ? C11A C12A H12A 120.5 . . ? C13A C12A H12A 120.5 . . ? C14A C13A C12A 119.8(3) . . ? C14A C13A C17A 121.5(4) . . ? C12A C13A C17A 118.6(4) . . ? C13A C14A C15A 120.9(3) . . ? C13A C14A H14A 119.5 . . ? C15A C14A H14A 119.5 . . ? C14A C15A C16A 119.8(3) . . ? C14A C15A H15A 120.1 . . ? C16A C15A H15A 120.1 . . ? C11A C16A C15A 120.2(3) . . ? C11A C16A H16A 119.9 . . ? C15A C16A H16A 119.9 . . ? C13A C17A H17A 109.5 . . ? C13A C17A H17B 109.5 . . ? H17A C17A H17B 109.5 . . ? C13A C17A H17C 109.5 . . ? H17A C17A H17C 109.5 . . ? H17B C17A H17C 109.5 . . ? N22A C21A C26A 123.7(3) . . ? N22A C21A C1A 117.4(3) . . ? C26A C21A C1A 118.9(3) . . ? C23A N22A C21A 115.7(3) . . ? N22A C23A C24A 124.5(3) . . ? N22A C23A H23A 117.7 . . ? C24A C23A H23A 117.7 . . ? C25A C24A C23A 118.6(3) . . ? C25A C24A H24A 120.7 . . ? C23A C24A H24A 120.7 . . ? C24A C25A C26A 118.4(3) . . ? C24A C25A H25A 120.8 . . ? C26A C25A H25A 120.8 . . ? C21A C26A C25A 119.0(3) . . ? C21A C26A H26A 120.5 . . ? C25A C26A H26A 120.5 . . ? C1B N1B C11B 128.2(3) . . ? C1B N1B H1B 115.8(16) . . ? C11B N1B H1B 115.8(16) . . ? O1B C1B N1B 125.4(3) . . ? O1B C1B C21B 120.0(3) . . ? N1B C1B C21B 114.6(3) . . ? C12B C11B C16B 119.4(3) . . ? C12B C11B N1B 122.6(3) . . ? C16B C11B N1B 117.9(3) . . ? C11B C12B C13B 120.8(3) . . ? C11B C12B H12B 119.6 . . ? C13B C12B H12B 119.6 . . ? C14B C13B C12B 119.6(3) . . ? C14B C13B C17B 119.7(3) . . ? C12B C13B C17B 120.7(3) . . ? C13B C14B C15B 119.2(3) . . ? C13B C14B H14B 120.4 . . ? C15B C14B H14B 120.4 . . ? C14B C15B C16B 121.3(3) . . ? C14B C15B H15B 119.3 . . ? C16B C15B H15B 119.3 . . ? C11B C16B C15B 119.6(3) . . ? C11B C16B H16B 120.2 . . ? C15B C16B H16B 120.2 . . ? C13B C17B H17D 109.5 . . ? C13B C17B H17E 109.5 . . ? H17D C17B H17E 109.5 . . ? C13B C17B H17F 109.5 . . ? H17D C17B H17F 109.5 . . ? H17E C17B H17F 109.5 . . ? N22B C21B C26B 124.2(3) . . ? N22B C21B C1B 117.4(3) . . ? C26B C21B C1B 118.3(3) . . ? C21B N22B C23B 116.5(3) . . ? N22B C23B C24B 123.3(4) . . ? N22B C23B H23B 118.4 . . ? C24B C23B H23B 118.4 . . ? C23B C24B C25B 119.5(4) . . ? C23B C24B H24B 120.2 . . ? C25B C24B H24B 120.2 . . ? C24B C25B C26B 118.3(4) . . ? C24B C25B H25B 120.9 . . ? C26B C25B H25B 120.9 . . ? C21B C26B C25B 118.2(3) . . ? C21B C26B H26B 120.9 . . ? C25B C26B H26B 120.9 . . ? 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 C11A N1A C1A O1A 4.3(4) . . . . ? C11A N1A C1A C21A -173.8(2) . . . . ? C1A N1A C11A C16A 162.2(3) . . . . ? C1A N1A C11A C12A -20.6(4) . . . . ? C16A C11A C12A C13A -1.1(4) . . . . ? N1A C11A C12A C13A -178.2(2) . . . . ? C11A C12A C13A C14A 0.5(4) . . . . ? C11A C12A C13A C17A 179.1(3) . . . . ? C12A C13A C14A C15A 0.5(5) . . . . ? C17A C13A C14A C15A -178.1(3) . . . . ? C13A C14A C15A C16A -1.0(5) . . . . ? C12A C11A C16A C15A 0.6(4) . . . . ? N1A C11A C16A C15A 177.9(2) . . . . ? C14A C15A C16A C11A 0.4(4) . . . . ? O1A C1A C21A N22A -176.0(3) . . . . ? N1A C1A C21A N22A 2.2(3) . . . . ? O1A C1A C21A C26A 2.2(4) . . . . ? N1A C1A C21A C26A -179.7(3) . . . . ? C26A C21A N22A C23A -0.6(4) . . . . ? C1A C21A N22A C23A 177.5(2) . . . . ? C21A N22A C23A C24A -1.5(5) . . . . ? N22A C23A C24A C25A 2.6(6) . . . . ? C23A C24A C25A C26A -1.6(5) . . . . ? N22A C21A C26A C25A 1.5(4) . . . . ? C1A C21A C26A C25A -176.6(3) . . . . ? C24A C25A C26A C21A -0.3(5) . . . . ? C11B N1B C1B O1B 4.0(5) . . . . ? C11B N1B C1B C21B -176.1(2) . . . . ? C1B N1B C11B C12B -10.3(4) . . . . ? C1B N1B C11B C16B 171.4(3) . . . . ? C16B C11B C12B C13B -1.7(4) . . . . ? N1B C11B C12B C13B -180.0(3) . . . . ? C11B C12B C13B C14B 1.0(4) . . . . ? C11B C12B C13B C17B -178.1(3) . . . . ? C12B C13B C14B C15B 0.4(5) . . . . ? C17B C13B C14B C15B 179.4(3) . . . . ? C13B C14B C15B C16B -0.9(5) . . . . ? C12B C11B C16B C15B 1.1(4) . . . . ? N1B C11B C16B C15B 179.5(3) . . . . ? C14B C15B C16B C11B 0.2(5) . . . . ? O1B C1B C21B N22B -162.6(3) . . . . ? N1B C1B C21B N22B 17.5(4) . . . . ? O1B C1B C21B C26B 14.8(4) . . . . ? N1B C1B C21B C26B -165.1(3) . . . . ? C26B C21B N22B C23B 0.0(4) . . . . ? C1B C21B N22B C23B 177.3(3) . . . . ? C21B N22B C23B C24B 0.8(5) . . . . ? N22B C23B C24B C25B -0.3(6) . . . . ? C23B C24B C25B C26B -1.0(6) . . . . ? N22B C21B C26B C25B -1.3(5) . . . . ? C1B C21B C26B C25B -178.5(3) . . . . ? C24B C25B C26B C21B 1.7(5) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # # Hydrogen bonding scheme # ======== ======= ====== # # D H A D-H H...A D...A D-H...A symm publ # - - - --- ----- ----- ------- ---- ---- N1A H1A O1B 0.93(2) 2.41(2) 3.241(3) 148(2) 2 yes N1B H1B O1A 0.87(2) 2.32(2) 3.132(3) 155(2) . yes N1A H1A N22A 0.93(2) 2.18(2) 2.683(4) 112.9(18) . yes N1B H1B N22B 0.87(2) 2.28(2) 2.703(4) 109.5(19) . yes C12A H12A O1A 0.93 2.29 2.862(4) 120 . yes C14B H14B Cg1 0.93 2.66 3.543(4) 160 2_645 yes # C12B H12B O1B 0.93 2.25 2.869(4) 123.4 . # C14B H14B C11A 0.93 2.93 3.646(4) 135.2 2_645 # C14B H14B C12A 0.93 3.02 3.716(4) 133.0 2_645 # C14B H14B C13A 0.93 3.09 3.882(5) 143.8 2_645 # C14B H14B C14A 0.93 3.06 3.958(5) 162.1 2_645 # C14B H14B C15A 0.93 2.96 3.875(5) 170.1 2_645 # C14B H14B C16A 0.93 2.89 3.722(4) 149.8 2_645 # Cg1 is the C~6~ aromatic ring centroid located # at site 2_645 OR [1-X,-1/2+Y,-Z] # Complete details for the C-H...\p(arene) interaction #============================================================ data_NooM_[10-075] _database_code_depnum_ccdc_archive 'CCDC 809626' #TrackingRef 'NxxM_5-Cl-NoxM_fin.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common NooM _chemical_melting_point 338 _chemical_formula_moiety 'C13 H12 N2 O' _chemical_formula_sum 'C13 H12 N2 O' _chemical_formula_weight 212.25 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 Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 7.7696(2) _cell_length_b 17.6232(3) _cell_length_c 8.8462(3) _cell_angle_alpha 90.00 _cell_angle_beta 114.817(4) _cell_angle_gamma 90.00 _cell_volume 1099.41(5) _cell_formula_units_Z 4 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 3103 _cell_measurement_theta_min 3.7 _cell_measurement_theta_max 27.3 _exptl_crystal_description Needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.282 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type Analytical _exptl_absorpt_correction_T_min 0.964 _exptl_absorpt_correction_T_max 0.991 _exptl_absorpt_process_details '(ABSFAC, Clark and Reid, 1998)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Xcalibur, Sapphire3, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_standards_number 7790 _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 1 _diffrn_reflns_number 7586 _diffrn_reflns_av_R_equivalents 0.0212 _diffrn_reflns_av_sigmaI/netI 0.0293 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.43 _diffrn_reflns_theta_max 27.47 _diffrn_measured_fraction_theta_max 0.947 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _reflns_number_total 2389 _reflns_number_gt 1541 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008) and SORTX (McArdle, 1995)' _computing_molecular_graphics 'PLATON (Spek, 2009)' _computing_publication_material SHELXL97 _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 'w=1/[\s^2^(Fo^2^)+(0.0525P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.010(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2389 _refine_ls_number_parameters 151 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0613 _refine_ls_R_factor_gt 0.0365 _refine_ls_wR_factor_ref 0.0934 _refine_ls_wR_factor_gt 0.0881 _refine_ls_goodness_of_fit_ref 0.926 _refine_ls_restrained_S_all 0.926 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.137 _refine_diff_density_min -0.106 _refine_diff_density_rms 0.024 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.41793(14) 0.59737(5) 0.16799(11) 0.0731(3) Uani 1 1 d . . . C1 C 0.33507(16) 0.56473(6) 0.03523(16) 0.0485(3) Uani 1 1 d . . . N1 N 0.25235(14) 0.49594(5) 0.01469(14) 0.0507(3) Uani 1 1 d . . . H1 H 0.1987(18) 0.4831(7) -0.0932(19) 0.063(4) Uiso 1 1 d . . . C11 C 0.23671(15) 0.44517(6) 0.13089(14) 0.0448(3) Uani 1 1 d . . . C12 C 0.14188(15) 0.37668(7) 0.06777(15) 0.0480(3) Uani 1 1 d . . . C13 C 0.12919(18) 0.32510(7) 0.18083(17) 0.0578(3) Uani 1 1 d . . . H13 H 0.0672 0.2792 0.1417 0.069 Uiso 1 1 calc R . . C14 C 0.20507(19) 0.33951(8) 0.34850(17) 0.0628(4) Uani 1 1 d . . . H14 H 0.1964 0.3034 0.4217 0.075 Uiso 1 1 calc R . . C15 C 0.29385(18) 0.40743(8) 0.40770(17) 0.0620(4) Uani 1 1 d . . . H15 H 0.3430 0.4179 0.5211 0.074 Uiso 1 1 calc R . . C16 C 0.31054(17) 0.46021(7) 0.29982(16) 0.0557(3) Uani 1 1 d . . . H16 H 0.3716 0.5061 0.3407 0.067 Uiso 1 1 calc R . . C17 C 0.05617(19) 0.36028(8) -0.11526(16) 0.0653(4) Uani 1 1 d . . . H17A H -0.0076 0.3122 -0.1356 0.098 Uiso 1 1 calc R . . H17B H 0.1544 0.3588 -0.1542 0.098 Uiso 1 1 calc R . . H17C H -0.0332 0.3994 -0.1733 0.098 Uiso 1 1 calc R . . C21 C 0.31377(16) 0.59981(6) -0.12638(15) 0.0473(3) Uani 1 1 d . . . N22 N 0.21755(14) 0.55958(6) -0.26448(13) 0.0555(3) Uani 1 1 d . . . C23 C 0.1950(2) 0.59075(8) -0.40828(17) 0.0666(4) Uani 1 1 d . . . H23 H 0.1292 0.5635 -0.5057 0.080 Uiso 1 1 calc R . . C24 C 0.2637(2) 0.66116(8) -0.42070(19) 0.0690(4) Uani 1 1 d . . . H24 H 0.2438 0.6809 -0.5242 0.083 Uiso 1 1 calc R . . C25 C 0.36204(19) 0.70191(8) -0.27827(18) 0.0642(4) Uani 1 1 d . . . H25 H 0.4096 0.7498 -0.2834 0.077 Uiso 1 1 calc R . . C26 C 0.38894(18) 0.67046(7) -0.12735(16) 0.0550(3) Uani 1 1 d . . . H26 H 0.4564 0.6964 -0.0284 0.066 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 O1 0.1015(7) 0.0579(6) 0.0499(6) -0.0031(4) 0.0219(5) -0.0188(5) C1 0.0525(7) 0.0426(7) 0.0487(8) 0.0009(6) 0.0194(6) 0.0038(5) N1 0.0617(6) 0.0450(6) 0.0418(7) 0.0002(5) 0.0182(5) -0.0017(5) C11 0.0440(6) 0.0434(7) 0.0455(7) 0.0031(5) 0.0174(5) 0.0034(5) C12 0.0456(6) 0.0437(7) 0.0525(8) -0.0015(5) 0.0185(5) 0.0046(5) C13 0.0585(7) 0.0479(7) 0.0670(9) 0.0001(6) 0.0263(7) -0.0066(6) C14 0.0652(8) 0.0632(9) 0.0625(9) 0.0113(7) 0.0291(7) -0.0062(7) C15 0.0638(8) 0.0701(9) 0.0486(8) 0.0030(7) 0.0202(6) -0.0098(7) C16 0.0577(7) 0.0548(8) 0.0493(8) -0.0005(6) 0.0171(6) -0.0096(6) C17 0.0759(9) 0.0536(8) 0.0596(9) -0.0099(6) 0.0216(7) -0.0033(7) C21 0.0478(6) 0.0450(7) 0.0513(8) 0.0034(5) 0.0230(6) 0.0097(5) N22 0.0646(6) 0.0547(6) 0.0479(7) 0.0030(5) 0.0243(5) 0.0052(5) C23 0.0801(9) 0.0690(10) 0.0505(9) 0.0030(7) 0.0273(7) 0.0036(7) C24 0.0821(10) 0.0718(10) 0.0582(9) 0.0165(8) 0.0345(8) 0.0094(8) C25 0.0738(9) 0.0525(8) 0.0758(11) 0.0142(7) 0.0407(8) 0.0063(7) C26 0.0616(7) 0.0478(7) 0.0593(8) 0.0019(6) 0.0291(6) 0.0045(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 O1 C1 1.2207(14) . ? C1 N1 1.3482(14) . ? C1 C21 1.5015(17) . ? N1 C11 1.4060(15) . ? N1 H1 0.896(14) . ? C11 C16 1.3831(16) . ? C11 C12 1.4022(16) . ? C12 C13 1.3853(17) . ? C12 C17 1.4978(17) . ? C13 C14 1.3704(18) . ? C13 H13 0.9300 . ? C14 C15 1.3710(18) . ? C14 H14 0.9300 . ? C15 C16 1.3771(17) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C21 N22 1.3368(15) . ? C21 C26 1.3769(17) . ? N22 C23 1.3280(16) . ? C23 C24 1.3733(19) . ? C23 H23 0.9300 . ? C24 C25 1.3707(19) . ? C24 H24 0.9300 . ? C25 C26 1.3780(17) . ? C25 H25 0.9300 . ? C26 H26 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 O1 C1 N1 125.63(12) . . ? O1 C1 C21 121.66(11) . . ? N1 C1 C21 112.71(11) . . ? C1 N1 C11 131.02(11) . . ? C1 N1 H1 110.7(8) . . ? C11 N1 H1 118.3(8) . . ? C16 C11 C12 120.36(11) . . ? C16 C11 N1 122.96(11) . . ? C12 C11 N1 116.67(11) . . ? C13 C12 C11 117.52(12) . . ? C13 C12 C17 121.32(11) . . ? C11 C12 C17 121.16(11) . . ? C14 C13 C12 122.09(12) . . ? C14 C13 H13 119.0 . . ? C12 C13 H13 119.0 . . ? C13 C14 C15 119.61(12) . . ? C13 C14 H14 120.2 . . ? C15 C14 H14 120.2 . . ? C14 C15 C16 120.24(13) . . ? C14 C15 H15 119.9 . . ? C16 C15 H15 119.9 . . ? C15 C16 C11 120.16(12) . . ? C15 C16 H16 119.9 . . ? C11 C16 H16 119.9 . . ? C12 C17 H17A 109.5 . . ? C12 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C12 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N22 C21 C26 123.35(12) . . ? N22 C21 C1 116.59(11) . . ? C26 C21 C1 120.05(11) . . ? C23 N22 C21 117.03(12) . . ? N22 C23 C24 123.43(13) . . ? N22 C23 H23 118.3 . . ? C24 C23 H23 118.3 . . ? C25 C24 C23 119.03(13) . . ? C25 C24 H24 120.5 . . ? C23 C24 H24 120.5 . . ? C24 C25 C26 118.63(13) . . ? C24 C25 H25 120.7 . . ? C26 C25 H25 120.7 . . ? C21 C26 C25 118.52(12) . . ? C21 C26 H26 120.7 . . ? C25 C26 H26 120.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 N1 C11 0.4(2) . . . . ? C21 C1 N1 C11 -178.85(10) . . . . ? C1 N1 C11 C16 0.38(19) . . . . ? C1 N1 C11 C12 -179.28(11) . . . . ? C16 C11 C12 C13 -1.25(16) . . . . ? N1 C11 C12 C13 178.42(10) . . . . ? C16 C11 C12 C17 178.25(11) . . . . ? N1 C11 C12 C17 -2.08(16) . . . . ? C11 C12 C13 C14 0.18(17) . . . . ? C17 C12 C13 C14 -179.32(12) . . . . ? C12 C13 C14 C15 1.17(19) . . . . ? C13 C14 C15 C16 -1.5(2) . . . . ? C14 C15 C16 C11 0.4(2) . . . . ? C12 C11 C16 C15 0.97(18) . . . . ? N1 C11 C16 C15 -178.67(11) . . . . ? O1 C1 C21 N22 -178.87(11) . . . . ? N1 C1 C21 N22 0.45(14) . . . . ? O1 C1 C21 C26 0.13(17) . . . . ? N1 C1 C21 C26 179.45(10) . . . . ? C26 C21 N22 C23 -0.16(17) . . . . ? C1 C21 N22 C23 178.80(10) . . . . ? C21 N22 C23 C24 -0.45(19) . . . . ? N22 C23 C24 C25 0.4(2) . . . . ? C23 C24 C25 C26 0.23(19) . . . . ? N22 C21 C26 C25 0.78(18) . . . . ? C1 C21 C26 C25 -178.14(10) . . . . ? C24 C25 C26 C21 -0.79(18) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # # Hydrogen bonding scheme # ======== ======= ====== # # D H A D-H H...A D...A D-H...A symm publ # - - - --- ----- ----- ------- ---- ---- N1 H1 N22 0.896(14) 2.079(13) 2.6209(15) 118.0(11) . yes C16 H16 O1 0.93 2.35 2.9524(16) 122 . yes # C15 H15 O1 0.93 2.61 3.4720(16) 155 3_666 yes #============================================================ # END of 3 x 3 isomer grid #============================================================ #============================================================ data_Cl_NopM_[10-024] _database_code_depnum_ccdc_archive 'CCDC 809627' #TrackingRef 'NxxM_5-Cl-NoxM_fin.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common Cl_NopM _chemical_melting_point 400 _chemical_formula_moiety 'C13 H11 Cl N2 O' _chemical_formula_sum 'C13 H11 Cl N2 O' _chemical_formula_weight 246.69 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P c a 21' _symmetry_space_group_name_Hall 'P 2c -2ac' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' _cell_length_a 7.36124(11) _cell_length_b 14.41068(19) _cell_length_c 11.21075(16) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1189.24(3) _cell_formula_units_Z 4 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 6263 _cell_measurement_theta_min 3.3 _cell_measurement_theta_max 27.8 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.378 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 512 _exptl_absorpt_coefficient_mu 0.305 _exptl_absorpt_correction_type Analytical _exptl_absorpt_correction_T_min 0.925 _exptl_absorpt_correction_T_max 0.953 _exptl_absorpt_process_details '(ABSFAC. Clark & Reid, 1998)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Xcalibur, Sapphire3, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_standards_number 8794 _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 1 _diffrn_reflns_number 8794 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0197 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.60 _diffrn_reflns_theta_max 27.83 _diffrn_measured_fraction_theta_max 0.962 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _reflns_number_total 8794 _reflns_number_gt 7810 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008) and SORTX (McArdle, 1995)' _computing_molecular_graphics 'PLATON (Spek, 2009)' _computing_publication_material SHELXL97 _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 'w=1/[\s^2^(Fo^2^)+(0.0419P)^2^] 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, 1983)' _refine_ls_abs_structure_Flack 0.00(4) _refine_ls_number_reflns 8794 _refine_ls_number_parameters 160 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0297 _refine_ls_R_factor_gt 0.0260 _refine_ls_wR_factor_ref 0.0652 _refine_ls_wR_factor_gt 0.0639 _refine_ls_goodness_of_fit_ref 0.983 _refine_ls_restrained_S_all 0.983 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.10 _refine_diff_density_min -0.16 _refine_diff_density_rms 0.033 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 Cl1 Cl 0.19243(3) -0.205466(16) 0.62082(3) 0.06396(8) Uani 1 1 d . . . O1 O 0.19031(9) 0.16431(4) 0.65205(5) 0.05522(18) Uani 1 1 d . . . N1 N 0.11121(11) 0.19533(5) 0.84497(7) 0.04434(18) Uani 1 1 d . . . H1 H 0.0890(13) 0.1653(6) 0.9154(8) 0.049(3) Uiso 1 1 d . . . C1 C 0.14627(11) 0.13886(6) 0.75231(8) 0.04014(19) Uani 1 1 d . . . C11 C 0.11772(12) 0.29320(5) 0.84940(8) 0.04068(19) Uani 1 1 d . . . C12 C 0.10001(14) 0.34878(6) 0.74838(9) 0.0516(2) Uani 1 1 d . . . H12 H 0.0866 0.3222 0.6733 0.062 Uiso 1 1 calc R . . C13 C 0.10264(13) 0.44407(6) 0.76153(10) 0.0563(3) Uani 1 1 d . . . H13 H 0.0909 0.4809 0.6939 0.068 Uiso 1 1 calc R . . C14 C 0.12194(12) 0.48681(6) 0.87073(10) 0.0519(2) Uani 1 1 d . . . C15 C 0.13884(12) 0.43004(7) 0.97031(9) 0.0534(2) Uani 1 1 d . . . H15 H 0.1512 0.4568 1.0453 0.064 Uiso 1 1 calc R . . C16 C 0.13758(12) 0.33446(6) 0.95993(8) 0.0482(2) Uani 1 1 d . . . H16 H 0.1502 0.2977 1.0276 0.058 Uiso 1 1 calc R . . C17 C 0.12416(15) 0.59130(7) 0.88261(12) 0.0736(4) Uani 1 1 d . . . H17A H 0.2367 0.6151 0.8520 0.110 Uiso 1 1 calc R . . H17B H 0.1123 0.6080 0.9651 0.110 Uiso 1 1 calc R . . H17C H 0.0249 0.6172 0.8382 0.110 Uiso 1 1 calc R . . C21 C 0.12476(11) 0.03752(6) 0.78142(7) 0.03846(19) Uani 1 1 d . . . N22 N 0.06415(9) 0.01622(5) 0.88940(7) 0.04436(18) Uani 1 1 d . . . C23 C 0.04236(13) -0.07408(6) 0.91456(8) 0.0514(2) Uani 1 1 d . . . H23 H -0.0008 -0.0903 0.9897 0.062 Uiso 1 1 calc R . . C24 C 0.08071(13) -0.14405(6) 0.83460(9) 0.0490(2) Uani 1 1 d . . . H24 H 0.0643 -0.2060 0.8551 0.059 Uiso 1 1 calc R . . C25 C 0.14347(11) -0.11967(6) 0.72433(8) 0.0429(2) Uani 1 1 d . . . C26 C 0.16636(10) -0.02765(6) 0.69463(8) 0.04037(19) Uani 1 1 d . . . H26 H 0.2079 -0.0100 0.6196 0.048 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 Cl1 0.08177(17) 0.04305(12) 0.06704(15) -0.01309(13) 0.00632(15) 0.00092(11) O1 0.0782(5) 0.0406(3) 0.0468(4) 0.0039(3) 0.0032(3) -0.0037(3) N1 0.0577(5) 0.0329(4) 0.0424(4) 0.0053(4) 0.0041(4) -0.0004(3) C1 0.0427(5) 0.0367(4) 0.0410(5) 0.0029(4) -0.0052(4) 0.0015(4) C11 0.0428(5) 0.0325(4) 0.0467(5) 0.0039(4) 0.0032(4) 0.0001(4) C12 0.0668(6) 0.0426(5) 0.0453(5) 0.0049(4) 0.0013(5) 0.0059(4) C13 0.0661(6) 0.0402(5) 0.0628(6) 0.0167(5) 0.0067(5) 0.0073(5) C14 0.0428(5) 0.0355(5) 0.0775(7) 0.0004(5) 0.0088(5) 0.0006(4) C15 0.0557(5) 0.0450(6) 0.0596(6) -0.0092(5) 0.0031(5) -0.0040(4) C16 0.0534(5) 0.0429(5) 0.0483(5) 0.0040(4) 0.0011(4) -0.0008(4) C17 0.0719(7) 0.0367(6) 0.1123(11) -0.0016(6) 0.0148(7) 0.0007(5) C21 0.0349(4) 0.0373(5) 0.0432(5) 0.0022(4) -0.0055(4) -0.0021(3) N22 0.0500(5) 0.0381(4) 0.0449(4) 0.0033(3) -0.0008(3) -0.0022(3) C23 0.0634(6) 0.0448(5) 0.0459(5) 0.0073(4) 0.0033(5) -0.0040(5) C24 0.0564(6) 0.0325(4) 0.0580(6) 0.0056(4) -0.0036(5) -0.0024(4) C25 0.0413(5) 0.0392(5) 0.0481(5) -0.0058(4) -0.0036(4) 0.0004(4) C26 0.0445(5) 0.0367(5) 0.0400(5) 0.0004(4) -0.0028(4) 0.0005(3) _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 Cl1 C25 1.7335(9) . ? O1 C1 1.2260(10) . ? N1 C1 1.3446(12) . ? N1 C11 1.4121(10) . ? N1 H1 0.915(9) . ? C1 C21 1.5048(12) . ? C11 C16 1.3822(12) . ? C11 C12 1.3932(12) . ? C12 C13 1.3812(13) . ? C12 H12 0.9300 . ? C13 C14 1.3778(15) . ? C13 H13 0.9300 . ? C14 C15 1.3897(13) . ? C14 C17 1.5116(13) . ? C15 C16 1.3823(13) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C21 N22 1.3261(10) . ? C21 C26 1.3866(11) . ? N22 C23 1.3411(10) . ? C23 C24 1.3783(13) . ? C23 H23 0.9300 . ? C24 C25 1.3657(13) . ? C24 H24 0.9300 . ? C25 C26 1.3775(11) . ? C26 H26 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 C1 N1 C11 128.69(8) . . ? C1 N1 H1 114.5(6) . . ? C11 N1 H1 116.6(6) . . ? O1 C1 N1 125.32(8) . . ? O1 C1 C21 121.13(8) . . ? N1 C1 C21 113.55(7) . . ? C16 C11 C12 119.43(8) . . ? C16 C11 N1 117.69(8) . . ? C12 C11 N1 122.85(8) . . ? C13 C12 C11 118.91(9) . . ? C13 C12 H12 120.5 . . ? C11 C12 H12 120.5 . . ? C14 C13 C12 122.74(9) . . ? C14 C13 H13 118.6 . . ? C12 C13 H13 118.6 . . ? C13 C14 C15 117.37(8) . . ? C13 C14 C17 121.65(10) . . ? C15 C14 C17 120.98(10) . . ? C16 C15 C14 121.23(9) . . ? C16 C15 H15 119.4 . . ? C14 C15 H15 119.4 . . ? C11 C16 C15 120.32(9) . . ? C11 C16 H16 119.8 . . ? C15 C16 H16 119.8 . . ? C14 C17 H17A 109.5 . . ? C14 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C14 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N22 C21 C26 123.92(8) . . ? N22 C21 C1 117.26(7) . . ? C26 C21 C1 118.81(7) . . ? C21 N22 C23 117.18(8) . . ? N22 C23 C24 123.26(9) . . ? N22 C23 H23 118.4 . . ? C24 C23 H23 118.4 . . ? C25 C24 C23 118.03(8) . . ? C25 C24 H24 121.0 . . ? C23 C24 H24 121.0 . . ? C24 C25 C26 120.51(8) . . ? C24 C25 Cl1 119.53(7) . . ? C26 C25 Cl1 119.96(7) . . ? C25 C26 C21 117.09(8) . . ? C25 C26 H26 121.5 . . ? C21 C26 H26 121.5 . . ? 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 C11 N1 C1 O1 -0.55(15) . . . . ? C11 N1 C1 C21 -179.93(8) . . . . ? C1 N1 C11 C16 -158.30(9) . . . . ? C1 N1 C11 C12 23.53(14) . . . . ? C16 C11 C12 C13 -0.06(14) . . . . ? N1 C11 C12 C13 178.09(8) . . . . ? C11 C12 C13 C14 -0.06(15) . . . . ? C12 C13 C14 C15 -0.13(14) . . . . ? C12 C13 C14 C17 -179.93(9) . . . . ? C13 C14 C15 C16 0.44(13) . . . . ? C17 C14 C15 C16 -179.76(9) . . . . ? C12 C11 C16 C15 0.37(13) . . . . ? N1 C11 C16 C15 -177.87(8) . . . . ? C14 C15 C16 C11 -0.57(13) . . . . ? O1 C1 C21 N22 -175.25(8) . . . . ? N1 C1 C21 N22 4.16(11) . . . . ? O1 C1 C21 C26 3.87(12) . . . . ? N1 C1 C21 C26 -176.71(7) . . . . ? C26 C21 N22 C23 -0.09(12) . . . . ? C1 C21 N22 C23 178.98(8) . . . . ? C21 N22 C23 C24 0.40(14) . . . . ? N22 C23 C24 C25 -0.19(15) . . . . ? C23 C24 C25 C26 -0.33(13) . . . . ? C23 C24 C25 Cl1 -179.72(7) . . . . ? C24 C25 C26 C21 0.60(12) . . . . ? Cl1 C25 C26 C21 179.99(6) . . . . ? N22 C21 C26 C25 -0.40(11) . . . . ? C1 C21 C26 C25 -179.46(7) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # # Hydrogen bonding scheme # ======== ======= ====== # # D H A D-H H...A D...A D-H...A symm publ # - - - --- ----- ----- ------- ---- ---- N1 H1 N22 0.915(9) 2.176(9) 2.6514(9) 111.5(7) . yes C12 H12 O1 0.93 2.41 2.9453(11) 116 . yes C23 H23 O1 0.93 2.53 3.4223(11) 161 2 yes C17 H17A Cg1 0.96 2.82 3.6699(12) 147 3_565 yes # C17 H17A C11 0.96 3.10 4.0137(14) 159.4 3_565 yes # C17 H17A C12 0.96 2.96 3.9090(15) 169.2 3_565 yes # C17 H17A C13 0.96 3.00 3.8089(15) 142.6 3_565 yes # C17 H17A C14 0.96 3.20 3.8356(14) 125.3 3_565 yes # C17 H17A C15 0.96 3.31 3.9262(15) 124.0 3_565 yes # C17 H17A C16 0.96 3.27 4.0225(15) 136.6 3_565 yes # Cg1 is the C~6~ aromatic ring centroids located at site 3_565 #============================================================ data_Cl_NomM_[10-096] _database_code_depnum_ccdc_archive 'CCDC 809628' #TrackingRef 'NxxM_5-Cl-NoxM_fin.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common Cl-NomM _chemical_melting_point 346 _chemical_formula_moiety 'C13 H11 Cl N2 O' _chemical_formula_sum 'C13 H11 Cl N2 O' _chemical_formula_weight 246.69 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 7.417(2) _cell_length_b 21.006(4) _cell_length_c 8.546(2) _cell_angle_alpha 90.00 _cell_angle_beta 115.28(3) _cell_angle_gamma 90.00 _cell_volume 1204.0(5) _cell_formula_units_Z 4 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 3103 _cell_measurement_theta_min 3.69 _cell_measurement_theta_max 27.35 _exptl_crystal_description Plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.53 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.361 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 512 _exptl_absorpt_coefficient_mu 0.301 _exptl_absorpt_correction_type Analytical _exptl_absorpt_correction_T_min 0.8567 _exptl_absorpt_correction_T_max 0.9866 _exptl_absorpt_process_details '(ABSFAC. Clark & Reid, 1998)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Xcalibur, Sapphire3, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_standards_number 7790 _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 1 _diffrn_reflns_number 8582 _diffrn_reflns_av_R_equivalents 0.0475 _diffrn_reflns_av_sigmaI/netI 0.0565 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.60 _diffrn_reflns_theta_max 27.13 _diffrn_measured_fraction_theta_max 0.960 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.994 _reflns_number_total 2583 _reflns_number_gt 1324 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _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 'w=1/[\s^2^(Fo^2^)+(0.1306P)^2^] 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 2583 _refine_ls_number_parameters 160 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1192 _refine_ls_R_factor_gt 0.0657 _refine_ls_wR_factor_ref 0.2332 _refine_ls_wR_factor_gt 0.2127 _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_restrained_S_all 1.004 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.323 _refine_diff_density_min -0.196 _refine_diff_density_rms 0.065 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 Cl1 Cl 0.25013(18) 0.49695(5) 0.25422(15) 0.0916(5) Uani 1 1 d . . . O1 O 0.5925(5) 0.69026(12) 0.6835(3) 0.0762(9) Uani 1 1 d . . . C1 C 0.5132(6) 0.71557(17) 0.5408(5) 0.0566(9) Uani 1 1 d . . . N1 N 0.5358(5) 0.77660(14) 0.5053(4) 0.0595(8) Uani 1 1 d . . . H1 H 0.478(7) 0.788(2) 0.398(6) 0.084(14) Uiso 1 1 d . . . C11 C 0.6424(6) 0.82654(16) 0.6195(5) 0.0549(9) Uani 1 1 d . . . C12 C 0.7700(5) 0.81833(19) 0.7919(5) 0.0572(9) Uani 1 1 d . . . H12 H 0.7942 0.7774 0.8375 0.069 Uiso 1 1 calc R . . C13 C 0.8636(6) 0.8695(2) 0.8995(5) 0.0633(10) Uani 1 1 d . . . C14 C 0.8247(6) 0.93000(19) 0.8262(6) 0.0676(11) Uani 1 1 d . . . H14 H 0.8840 0.9652 0.8948 0.081 Uiso 1 1 calc R . . C15 C 0.7001(7) 0.93850(18) 0.6542(6) 0.0710(11) Uani 1 1 d . . . H15 H 0.6763 0.9794 0.6078 0.085 Uiso 1 1 calc R . . C16 C 0.6102(6) 0.88726(18) 0.5498(5) 0.0656(10) Uani 1 1 d . . . H16 H 0.5282 0.8934 0.4330 0.079 Uiso 1 1 calc R . . C17 C 1.0011(7) 0.8592(2) 1.0868(6) 0.0824(13) Uani 1 1 d . . . H17A H 0.9325 0.8692 1.1568 0.124 Uiso 0.50 1 calc PR . . H17B H 1.1157 0.8862 1.1187 0.124 Uiso 0.50 1 calc PR . . H17C H 1.0430 0.8155 1.1045 0.124 Uiso 0.50 1 calc PR . . H17D H 1.1283 0.8447 1.0966 0.124 Uiso 0.50 1 calc PR . . H17E H 0.9451 0.8277 1.1347 0.124 Uiso 0.50 1 calc PR . . H17F H 1.0178 0.8985 1.1488 0.124 Uiso 0.50 1 calc PR . . C21 C 0.3758(5) 0.67803(16) 0.3845(5) 0.0533(9) Uani 1 1 d . . . N22 N 0.2642(4) 0.71056(14) 0.2410(4) 0.0603(8) Uani 1 1 d . . . C23 C 0.1459(6) 0.67629(19) 0.1027(6) 0.0714(11) Uani 1 1 d . . . H23 H 0.0656 0.6982 0.0025 0.086 Uiso 1 1 calc R . . C24 C 0.1355(6) 0.61139(19) 0.0992(5) 0.0693(11) Uani 1 1 d . . . H24 H 0.0529 0.5895 -0.0003 0.083 Uiso 1 1 calc R . . C25 C 0.2527(5) 0.57990(18) 0.2493(5) 0.0600(10) Uani 1 1 d . . . C26 C 0.3744(6) 0.61272(16) 0.3966(5) 0.0570(9) Uani 1 1 d . . . H26 H 0.4518 0.5917 0.4993 0.068 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 Cl1 0.1160(11) 0.0529(6) 0.0881(9) -0.0107(5) 0.0265(8) -0.0095(6) O1 0.113(2) 0.0614(15) 0.0465(16) 0.0006(12) 0.0266(16) -0.0028(15) C1 0.069(2) 0.058(2) 0.047(2) -0.0024(17) 0.0294(19) 0.0010(18) N1 0.081(2) 0.0509(17) 0.0460(18) -0.0027(14) 0.0264(17) -0.0041(15) C11 0.065(2) 0.058(2) 0.046(2) -0.0031(16) 0.0274(18) 0.0003(18) C12 0.059(2) 0.058(2) 0.057(2) -0.0019(17) 0.027(2) 0.0014(17) C13 0.060(2) 0.074(3) 0.055(2) -0.007(2) 0.025(2) -0.003(2) C14 0.071(2) 0.057(2) 0.065(3) -0.012(2) 0.020(2) -0.0093(19) C15 0.084(3) 0.047(2) 0.070(3) -0.0009(19) 0.022(2) -0.005(2) C16 0.074(3) 0.061(2) 0.054(2) 0.0028(18) 0.020(2) -0.0038(19) C17 0.088(3) 0.088(3) 0.057(3) -0.009(2) 0.017(2) -0.006(2) C21 0.063(2) 0.0534(19) 0.048(2) -0.0031(16) 0.0278(18) -0.0035(17) N22 0.066(2) 0.0506(17) 0.0544(19) 0.0001(14) 0.0157(17) 0.0002(14) C23 0.072(3) 0.067(2) 0.054(2) 0.006(2) 0.007(2) 0.004(2) C24 0.069(2) 0.070(3) 0.057(2) -0.008(2) 0.015(2) -0.009(2) C25 0.068(2) 0.052(2) 0.057(2) -0.0081(17) 0.024(2) -0.0063(17) C26 0.069(2) 0.052(2) 0.051(2) 0.0007(16) 0.0263(19) 0.0016(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C25 1.743(4) . ? O1 C1 1.226(4) . ? C1 N1 1.344(5) . ? C1 C21 1.510(5) . ? N1 C11 1.421(5) . ? N1 H1 0.86(5) . ? C11 C12 1.380(5) . ? C11 C16 1.385(5) . ? C12 C13 1.392(5) . ? C12 H12 0.9300 . ? C13 C14 1.391(6) . ? C13 C17 1.502(6) . ? C14 C15 1.373(7) . ? C14 H14 0.9300 . ? C15 C16 1.375(6) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C17 H17D 0.9600 . ? C17 H17E 0.9600 . ? C17 H17F 0.9600 . ? C21 N22 1.338(4) . ? C21 C26 1.376(5) . ? N22 C23 1.341(5) . ? C23 C24 1.365(6) . ? C23 H23 0.9300 . ? C24 C25 1.373(5) . ? C24 H24 0.9300 . ? C25 C26 1.380(5) . ? C26 H26 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 O1 C1 N1 125.8(4) . . ? O1 C1 C21 120.6(3) . . ? N1 C1 C21 113.6(3) . . ? C1 N1 C11 129.4(3) . . ? C1 N1 H1 117(3) . . ? C11 N1 H1 113(3) . . ? C12 C11 C16 119.2(3) . . ? C12 C11 N1 124.6(3) . . ? C16 C11 N1 116.2(3) . . ? C11 C12 C13 122.0(4) . . ? C11 C12 H12 119.0 . . ? C13 C12 H12 119.0 . . ? C14 C13 C12 117.3(4) . . ? C14 C13 C17 121.8(4) . . ? C12 C13 C17 120.8(4) . . ? C15 C14 C13 121.0(4) . . ? C15 C14 H14 119.5 . . ? C13 C14 H14 119.5 . . ? C14 C15 C16 120.7(3) . . ? C14 C15 H15 119.6 . . ? C16 C15 H15 119.6 . . ? C15 C16 C11 119.7(4) . . ? C15 C16 H16 120.2 . . ? C11 C16 H16 120.2 . . ? C13 C17 H17A 109.5 . . ? C13 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C13 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C13 C17 H17D 109.5 . . ? H17A C17 H17D 141.1 . . ? H17B C17 H17D 56.3 . . ? H17C C17 H17D 56.3 . . ? C13 C17 H17E 109.5 . . ? H17A C17 H17E 56.3 . . ? H17B C17 H17E 141.1 . . ? H17C C17 H17E 56.3 . . ? H17D C17 H17E 109.5 . . ? C13 C17 H17F 109.5 . . ? H17A C17 H17F 56.3 . . ? H17B C17 H17F 56.3 . . ? H17C C17 H17F 141.1 . . ? H17D C17 H17F 109.5 . . ? H17E C17 H17F 109.5 . . ? N22 C21 C26 123.8(3) . . ? N22 C21 C1 117.6(3) . . ? C26 C21 C1 118.6(3) . . ? C21 N22 C23 116.7(3) . . ? N22 C23 C24 124.4(4) . . ? N22 C23 H23 117.8 . . ? C24 C23 H23 117.8 . . ? C23 C24 C25 117.0(4) . . ? C23 C24 H24 121.5 . . ? C25 C24 H24 121.5 . . ? C24 C25 C26 121.2(4) . . ? C24 C25 Cl1 119.7(3) . . ? C26 C25 Cl1 119.1(3) . . ? C21 C26 C25 116.9(3) . . ? C21 C26 H26 121.5 . . ? C25 C26 H26 121.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 N1 C11 -4.1(6) . . . . ? C21 C1 N1 C11 175.9(3) . . . . ? C1 N1 C11 C12 10.0(6) . . . . ? C1 N1 C11 C16 -168.9(4) . . . . ? C16 C11 C12 C13 1.8(6) . . . . ? N1 C11 C12 C13 -177.1(3) . . . . ? C11 C12 C13 C14 -0.4(6) . . . . ? C11 C12 C13 C17 179.7(4) . . . . ? C12 C13 C14 C15 -0.6(6) . . . . ? C17 C13 C14 C15 179.3(4) . . . . ? C13 C14 C15 C16 0.1(7) . . . . ? C14 C15 C16 C11 1.3(7) . . . . ? C12 C11 C16 C15 -2.2(6) . . . . ? N1 C11 C16 C15 176.8(4) . . . . ? O1 C1 C21 N22 167.2(3) . . . . ? N1 C1 C21 N22 -12.8(5) . . . . ? O1 C1 C21 C26 -13.7(5) . . . . ? N1 C1 C21 C26 166.3(3) . . . . ? C26 C21 N22 C23 -0.2(5) . . . . ? C1 C21 N22 C23 178.8(3) . . . . ? C21 N22 C23 C24 -1.1(6) . . . . ? N22 C23 C24 C25 1.1(7) . . . . ? C23 C24 C25 C26 0.3(6) . . . . ? C23 C24 C25 Cl1 -179.2(3) . . . . ? N22 C21 C26 C25 1.4(5) . . . . ? C1 C21 C26 C25 -177.6(3) . . . . ? C24 C25 C26 C21 -1.4(5) . . . . ? Cl1 C25 C26 C21 178.0(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # # Hydrogen bonding scheme # ======== ======= ====== # # D H A D-H H...A D...A D-H...A symm publ # - - - --- ----- ----- ------- ---- ---- N1 H1 N22 0.86(5) 2.27(4) 2.683(4) 109(4) . yes N1 H1 O1 0.86(5) 2.37(5) 3.035(4) 134(4) 4_575 yes C12 H12 O1 0.93 2.37 2.964(5) 121.2 . yes # Contact from C21...C12_[4_575] at 3.34 Angstroms #============================================================ data_Cl_NooM_Mo_[10-012] _database_code_depnum_ccdc_archive 'CCDC 809629' #TrackingRef 'NxxM_5-Cl-NoxM_fin.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common Cl_NooM _chemical_melting_point 401 _chemical_formula_moiety 'C13 H11 Cl N2 O' _chemical_formula_sum 'C13 H11 Cl N2 O' _chemical_formula_weight 246.69 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.3288(6) _cell_length_b 7.4392(5) _cell_length_c 21.5025(14) _cell_angle_alpha 90.00 _cell_angle_beta 91.481(7) _cell_angle_gamma 90.00 _cell_volume 1171.93(15) _cell_formula_units_Z 4 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 4669 _cell_measurement_theta_min 3.3 _cell_measurement_theta_max 29.2 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.398 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 512 _exptl_absorpt_coefficient_mu 0.309 _exptl_absorpt_correction_type Analytical _exptl_absorpt_correction_T_min 0.889 _exptl_absorpt_correction_T_max 0.970 _exptl_absorpt_process_details '(ABSFAC, Clark and Reid, 1998)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Xcalibur, Sapphire3, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_standards_number 9725 _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 1 _diffrn_reflns_number 9725 _diffrn_reflns_av_R_equivalents 0.0171 _diffrn_reflns_av_sigmaI/netI 0.0198 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 3.33 _diffrn_reflns_theta_max 29.22 _diffrn_measured_fraction_theta_max 0.956 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.998 _reflns_number_total 3040 _reflns_number_gt 2199 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008) and SORTX (McArdle, 1995)' _computing_molecular_graphics 'PLATON (Spek, 2009)' _computing_publication_material SHELXL97 _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 'w=1/[\s^2^(Fo^2^)+(0.0519P)^2^+0.0738P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0011(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3040 _refine_ls_number_parameters 160 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0531 _refine_ls_R_factor_gt 0.0375 _refine_ls_wR_factor_ref 0.1034 _refine_ls_wR_factor_gt 0.0990 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.19 _refine_diff_density_min -0.22 _refine_diff_density_rms 0.034 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 Cl1 Cl 0.37267(7) -0.27148(6) 0.248000(17) 0.07224(17) Uani 1 1 d . . . O1 O 0.21051(18) 0.16962(14) 0.43126(5) 0.0698(3) Uani 1 1 d . . . N1 N 0.24048(16) 0.00528(15) 0.52072(5) 0.0440(3) Uani 1 1 d . . . H1 H 0.272(2) -0.102(2) 0.5315(7) 0.048(4) Uiso 1 1 d . . . C1 C 0.24756(18) 0.03092(16) 0.45872(6) 0.0436(3) Uani 1 1 d . . . C11 C 0.19212(17) 0.12596(16) 0.56801(6) 0.0417(3) Uani 1 1 d . . . C12 C 0.20985(17) 0.06479(18) 0.62960(6) 0.0456(3) Uani 1 1 d . . . C13 C 0.1619(2) 0.1822(2) 0.67671(7) 0.0566(4) Uani 1 1 d . . . H13 H 0.1729 0.1443 0.7178 0.068 Uiso 1 1 calc R . . C14 C 0.0985(2) 0.3533(2) 0.66422(8) 0.0609(4) Uani 1 1 d . . . H14 H 0.0679 0.4296 0.6966 0.073 Uiso 1 1 calc R . . C15 C 0.0807(2) 0.4102(2) 0.60360(8) 0.0586(4) Uani 1 1 d . . . H15 H 0.0365 0.5249 0.5950 0.070 Uiso 1 1 calc R . . C16 C 0.12814(19) 0.29841(18) 0.55534(7) 0.0511(3) Uani 1 1 d . . . H16 H 0.1173 0.3384 0.5144 0.061 Uiso 1 1 calc R . . C17 C 0.2770(2) -0.1211(2) 0.64462(7) 0.0607(4) Uani 1 1 d . . . H17A H 0.2874 -0.1355 0.6889 0.091 Uiso 1 1 calc R . . H17B H 0.3943 -0.1390 0.6267 0.091 Uiso 1 1 calc R . . H17C H 0.1923 -0.2079 0.6278 0.091 Uiso 1 1 calc R . . C21 C 0.30789(17) -0.13330(16) 0.42393(6) 0.0389(3) Uani 1 1 d . . . N22 N 0.35376(15) -0.27982(14) 0.45700(5) 0.0446(3) Uani 1 1 d . . . C23 C 0.4046(2) -0.42392(19) 0.42501(7) 0.0510(3) Uani 1 1 d . . . H23 H 0.4368 -0.5271 0.4471 0.061 Uiso 1 1 calc R . . C24 C 0.41234(19) -0.42919(19) 0.36078(7) 0.0504(3) Uani 1 1 d . . . H24 H 0.4482 -0.5328 0.3402 0.060 Uiso 1 1 calc R . . C25 C 0.36545(19) -0.27664(18) 0.32860(6) 0.0457(3) Uani 1 1 d . . . C26 C 0.31107(18) -0.12553(17) 0.35984(6) 0.0443(3) Uani 1 1 d . . . H26 H 0.2775 -0.0214 0.3385 0.053 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 Cl1 0.1013(4) 0.0735(3) 0.0423(2) -0.00999(17) 0.0081(2) -0.0088(2) O1 0.1175(10) 0.0382(5) 0.0537(6) 0.0038(4) 0.0044(6) 0.0101(6) N1 0.0547(7) 0.0346(5) 0.0427(6) -0.0023(4) 0.0023(5) 0.0015(5) C1 0.0491(7) 0.0370(6) 0.0446(7) -0.0001(5) -0.0002(6) -0.0052(5) C11 0.0381(6) 0.0389(6) 0.0481(7) -0.0080(5) 0.0021(5) -0.0060(5) C12 0.0422(7) 0.0467(7) 0.0481(7) -0.0056(6) 0.0028(5) -0.0096(6) C13 0.0539(8) 0.0650(9) 0.0510(8) -0.0155(7) 0.0048(6) -0.0079(7) C14 0.0502(8) 0.0651(10) 0.0677(10) -0.0291(8) 0.0038(7) -0.0023(7) C15 0.0485(8) 0.0447(7) 0.0822(11) -0.0184(7) -0.0032(7) 0.0015(6) C16 0.0495(8) 0.0438(7) 0.0597(8) -0.0070(6) -0.0032(6) -0.0011(6) C17 0.0820(11) 0.0519(8) 0.0484(8) 0.0028(6) 0.0035(7) -0.0066(7) C21 0.0388(6) 0.0357(6) 0.0421(6) -0.0006(5) -0.0002(5) -0.0046(5) N22 0.0496(6) 0.0400(6) 0.0440(6) 0.0007(4) -0.0027(5) 0.0003(5) C23 0.0585(8) 0.0415(7) 0.0526(8) 0.0011(6) -0.0037(6) 0.0058(6) C24 0.0513(8) 0.0445(7) 0.0553(8) -0.0098(6) 0.0004(6) 0.0027(6) C25 0.0464(7) 0.0505(7) 0.0404(7) -0.0055(6) 0.0014(5) -0.0084(6) C26 0.0490(7) 0.0410(7) 0.0427(7) 0.0021(5) -0.0015(5) -0.0053(5) _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 Cl1 C25 1.7356(14) . ? O1 C1 1.2160(15) . ? N1 C1 1.3491(17) . ? N1 C11 1.4086(16) . ? N1 H1 0.860(15) . ? C1 C21 1.5049(17) . ? C11 C16 1.3905(19) . ? C11 C12 1.4031(19) . ? C12 C13 1.3898(19) . ? C12 C17 1.500(2) . ? C13 C14 1.379(2) . ? C13 H13 0.9300 . ? C14 C15 1.374(2) . ? C14 H14 0.9300 . ? C15 C16 1.381(2) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C21 N22 1.3396(16) . ? C21 C26 1.3801(18) . ? N22 C23 1.3321(18) . ? C23 C24 1.384(2) . ? C23 H23 0.9300 . ? C24 C25 1.368(2) . ? C24 H24 0.9300 . ? C25 C26 1.3739(19) . ? C26 H26 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 C1 N1 C11 129.80(11) . . ? C1 N1 H1 112.4(10) . . ? C11 N1 H1 117.8(10) . . ? O1 C1 N1 125.88(12) . . ? O1 C1 C21 120.81(12) . . ? N1 C1 C21 113.31(11) . . ? C16 C11 C12 120.44(12) . . ? C16 C11 N1 122.44(12) . . ? C12 C11 N1 117.11(12) . . ? C13 C12 C11 117.71(13) . . ? C13 C12 C17 120.69(13) . . ? C11 C12 C17 121.60(12) . . ? C14 C13 C12 121.91(15) . . ? C14 C13 H13 119.0 . . ? C12 C13 H13 119.0 . . ? C15 C14 C13 119.51(14) . . ? C15 C14 H14 120.2 . . ? C13 C14 H14 120.2 . . ? C14 C15 C16 120.51(15) . . ? C14 C15 H15 119.7 . . ? C16 C15 H15 119.7 . . ? C15 C16 C11 119.90(14) . . ? C15 C16 H16 120.0 . . ? C11 C16 H16 120.0 . . ? C12 C17 H17A 109.5 . . ? C12 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C12 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N22 C21 C26 123.62(12) . . ? N22 C21 C1 118.01(11) . . ? C26 C21 C1 118.37(11) . . ? C23 N22 C21 116.76(11) . . ? N22 C23 C24 123.87(12) . . ? N22 C23 H23 118.1 . . ? C24 C23 H23 118.1 . . ? C25 C24 C23 117.70(12) . . ? C25 C24 H24 121.2 . . ? C23 C24 H24 121.2 . . ? C24 C25 C26 120.23(13) . . ? C24 C25 Cl1 120.63(11) . . ? C26 C25 Cl1 119.14(11) . . ? C25 C26 C21 117.82(12) . . ? C25 C26 H26 121.1 . . ? C21 C26 H26 121.1 . . ? 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 C1 O1 -0.5(2) . . . . ? C11 N1 C1 C21 179.52(12) . . . . ? C1 N1 C11 C16 4.8(2) . . . . ? C1 N1 C11 C12 -175.57(13) . . . . ? C16 C11 C12 C13 -0.14(19) . . . . ? N1 C11 C12 C13 -179.74(11) . . . . ? C16 C11 C12 C17 179.48(13) . . . . ? N1 C11 C12 C17 -0.12(19) . . . . ? C11 C12 C13 C14 0.1(2) . . . . ? C17 C12 C13 C14 -179.50(14) . . . . ? C12 C13 C14 C15 0.4(2) . . . . ? C13 C14 C15 C16 -0.9(2) . . . . ? C14 C15 C16 C11 0.8(2) . . . . ? C12 C11 C16 C15 -0.3(2) . . . . ? N1 C11 C16 C15 179.24(12) . . . . ? O1 C1 C21 N22 177.39(13) . . . . ? N1 C1 C21 N22 -2.61(16) . . . . ? O1 C1 C21 C26 -3.30(19) . . . . ? N1 C1 C21 C26 176.70(12) . . . . ? C26 C21 N22 C23 -0.03(19) . . . . ? C1 C21 N22 C23 179.24(11) . . . . ? C21 N22 C23 C24 0.1(2) . . . . ? N22 C23 C24 C25 0.2(2) . . . . ? C23 C24 C25 C26 -0.7(2) . . . . ? C23 C24 C25 Cl1 179.64(11) . . . . ? C24 C25 C26 C21 0.7(2) . . . . ? Cl1 C25 C26 C21 -179.57(10) . . . . ? N22 C21 C26 C25 -0.39(19) . . . . ? C1 C21 C26 C25 -179.65(11) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # # Hydrogen bonding scheme # ======== ======= ====== # # D H A D-H H...A D...A D-H...A symm publ # - - - --- ----- ----- ------- ---- ---- N1 H1 N22 0.860(15) 2.175(15) 2.6690(15) 116.3(12) . yes C16 H16 O1 0.93 2.30 2.9128(19) 123 . yes C26 H26 Cl1 0.93 2.83 3.7371(14) 165 2 yes #============================================================ # END of details for the 1 x 3 5_Cl_NoxM isomer grid #============================================================ data_10-086_NmpFM _database_code_depnum_ccdc_archive 'CCDC 809630' #TrackingRef 'NxxM_5-Cl-NoxM_fin.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common NmpFM _chemical_melting_point 406 _chemical_formula_moiety 'C13 H12 N2 O, C12 H9 F N2 O' _chemical_formula_sum 'C25 H21 F N4 O2' _chemical_formula_weight 428.46 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P n a 21' _symmetry_space_group_name_Hall 'P 2c -2n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 19.870(2) _cell_length_b 10.8608(9) _cell_length_c 4.9241(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1062.66(18) _cell_formula_units_Z 2 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 3516 _cell_measurement_theta_min 3.6 _cell_measurement_theta_max 27.2 _exptl_crystal_description Block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.51 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.339 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type Analytical _exptl_absorpt_correction_T_min 0.9540 _exptl_absorpt_correction_T_max 0.9884 _exptl_absorpt_process_details '(ABSFAC, Clark and Reid, 1998)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Xcalibur, Sapphire3, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_standards_number 3516 _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 1 _diffrn_reflns_number 6723 _diffrn_reflns_av_R_equivalents 0.0212 _diffrn_reflns_av_sigmaI/netI 0.0141 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 3.60 _diffrn_reflns_theta_max 27.24 _diffrn_measured_fraction_theta_max 0.966 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.997 _reflns_number_total 1286 _reflns_number_gt 1045 _reflns_threshold_expression I>2\(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008) and SORTX (McArdle, 1995)' _computing_molecular_graphics 'PLATON (Spek, 2009)' _computing_publication_material SHELXL97 _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 'w=1/[\s^2^(Fo^2^)+(0.0497P)^2^+0.0862P] 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, 1983)' _refine_ls_abs_structure_Flack 1(2) _refine_ls_number_reflns 1286 _refine_ls_number_parameters 159 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0448 _refine_ls_R_factor_gt 0.0348 _refine_ls_wR_factor_ref 0.0926 _refine_ls_wR_factor_gt 0.0888 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.107 _refine_diff_density_min -0.104 _refine_diff_density_rms 0.026 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 F14 F 0.2918(5) 0.3227(12) -0.755(3) 0.126(4) Uani 0.50 1 d P A -1 C17 C 0.2981(7) 0.3361(13) -0.771(3) 0.063(3) Uani 0.50 1 d P A -2 H17A H 0.2801 0.3121 -0.9443 0.094 Uiso 0.25 1 calc PR A -2 H17B H 0.3347 0.2826 -0.7240 0.094 Uiso 0.25 1 calc PR A -2 H17C H 0.3139 0.4194 -0.7810 0.094 Uiso 0.25 1 calc PR A -2 H17D H 0.3391 0.3640 -0.6886 0.094 Uiso 0.25 1 calc PR A -2 H17E H 0.2844 0.3935 -0.9089 0.094 Uiso 0.25 1 calc PR A -2 H17F H 0.3052 0.2567 -0.8518 0.094 Uiso 0.25 1 calc PR A -2 O1 O 0.07719(9) 0.11605(12) 0.1154(5) 0.0762(6) Uani 1 1 d . . . C1 C 0.06308(10) 0.22288(17) 0.1668(5) 0.0519(6) Uani 1 1 d . . . N1 N 0.09316(9) 0.31964(15) 0.0395(4) 0.0512(5) Uani 1 1 d . . . H1 H 0.0811(11) 0.394(2) 0.111(6) 0.066(7) Uiso 1 1 d . . . C11 C 0.14351(11) 0.31585(18) -0.1605(5) 0.0514(5) Uani 1 1 d . A . C12 C 0.16877(13) 0.2093(2) -0.2752(7) 0.0678(7) Uani 1 1 d . . . H12 H 0.1524 0.1330 -0.2201 0.081 Uiso 1 1 calc R . . C13 C 0.21837(14) 0.2158(3) -0.4718(7) 0.0755(8) Uani 1 1 d . A . H13 H 0.2350 0.1435 -0.5476 0.091 Uiso 1 1 calc R . . C14 C 0.24353(12) 0.3267(3) -0.5571(6) 0.0673(7) Uani 1 1 d . . . C15 C 0.21824(14) 0.4324(3) -0.4482(6) 0.0756(8) Uani 1 1 d . A . H15 H 0.2345 0.5082 -0.5070 0.091 Uiso 1 1 calc R . . C16 C 0.16908(13) 0.4281(2) -0.2526(6) 0.0679(7) Uani 1 1 d . . . H16 H 0.1525 0.5012 -0.1801 0.081 Uiso 1 1 calc R A . C21 C 0.00993(11) 0.25143(16) 0.3729(5) 0.0483(5) Uani 1 1 d . . . C22 C -0.01143(12) 0.36866(17) 0.4393(6) 0.0607(6) Uani 1 1 d . . . H22 H 0.0093 0.4346 0.3525 0.073 Uiso 1 1 calc R . . N23 N -0.05957(10) 0.39378(14) 0.6187(5) 0.0642(6) Uani 1 1 d . . . C24 C -0.08842(13) 0.2985(2) 0.7425(6) 0.0645(7) Uani 1 1 d . . . H24 H -0.1225 0.3138 0.8673 0.077 Uiso 1 1 calc R . . C25 C -0.07010(13) 0.1788(2) 0.6943(7) 0.0721(8) Uani 1 1 d . . . H25 H -0.0908 0.1147 0.7876 0.087 Uiso 1 1 calc R . . C26 C -0.02093(12) 0.15502(17) 0.5066(6) 0.0625(7) Uani 1 1 d . . . H26 H -0.0084 0.0743 0.4694 0.075 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 F14 0.095(6) 0.190(8) 0.092(6) -0.010(6) -0.005(5) 0.013(5) C17 0.050(4) 0.086(5) 0.052(5) -0.006(4) 0.024(4) 0.012(3) O1 0.1001(12) 0.0298(7) 0.0986(14) -0.0060(9) 0.0124(11) 0.0021(7) C1 0.0641(13) 0.0305(9) 0.0609(16) -0.0032(10) -0.0137(13) -0.0010(9) N1 0.0598(10) 0.0313(8) 0.0624(13) -0.0047(8) -0.0033(10) 0.0024(7) C11 0.0542(12) 0.0426(10) 0.0575(13) -0.0041(11) -0.0107(12) 0.0034(8) C12 0.0736(15) 0.0479(12) 0.0820(18) -0.0087(13) -0.0026(16) 0.0114(11) C13 0.0740(16) 0.0739(17) 0.0785(19) -0.0155(16) -0.0022(17) 0.0225(13) C14 0.0539(14) 0.0907(19) 0.0573(16) -0.0053(14) -0.0028(13) 0.0092(13) C15 0.0828(16) 0.0678(16) 0.0761(18) -0.0004(15) 0.0084(16) -0.0072(13) C16 0.0780(15) 0.0494(12) 0.0762(17) -0.0059(13) 0.0077(15) -0.0031(11) C21 0.0575(11) 0.0304(9) 0.0570(12) -0.0014(9) -0.0162(11) -0.0006(8) C22 0.0780(14) 0.0291(9) 0.0751(17) 0.0025(11) 0.0073(14) -0.0031(10) N23 0.0769(12) 0.0356(9) 0.0800(14) -0.0020(11) 0.0048(13) 0.0005(8) C24 0.0703(14) 0.0489(12) 0.0744(18) 0.0010(12) 0.0020(15) -0.0045(10) C25 0.0858(16) 0.0410(11) 0.090(2) 0.0095(14) 0.0082(17) -0.0074(11) C26 0.0774(15) 0.0281(9) 0.0818(18) 0.0024(11) 0.0009(15) -0.0014(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.220(2) . ? C1 N1 1.362(3) . ? C1 C21 1.497(3) . ? N1 C11 1.404(3) . ? N1 H1 0.92(3) . ? C11 C12 1.382(3) . ? C11 C16 1.396(3) . ? C12 C13 1.383(4) . ? C12 H12 0.9300 . ? C13 C14 1.370(4) . ? C13 H13 0.9300 . ? C14 C15 1.363(4) . ? C15 C16 1.373(4) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? F14 C14 1.367(11) . ? C17 C14 1.515(13) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C17 H17D 0.9600 . ? C17 H17E 0.9600 . ? C17 H17F 0.9600 . ? C21 C26 1.381(3) . ? C21 C22 1.381(3) . ? C22 N23 1.330(3) . ? C22 H22 0.9300 . ? N23 C24 1.331(3) . ? C24 C25 1.371(3) . ? C24 H24 0.9300 . ? C25 C26 1.369(4) . ? C25 H25 0.9300 . ? C26 H26 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 C14 C17 H17A 109.5 . . ? C14 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C14 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C14 C17 H17D 109.5 . . ? H17A C17 H17D 141.1 . . ? H17B C17 H17D 56.3 . . ? H17C C17 H17D 56.3 . . ? C14 C17 H17E 109.5 . . ? H17A C17 H17E 56.3 . . ? H17B C17 H17E 141.1 . . ? H17C C17 H17E 56.3 . . ? H17D C17 H17E 109.5 . . ? C14 C17 H17F 109.5 . . ? H17A C17 H17F 56.3 . . ? H17B C17 H17F 56.3 . . ? H17C C17 H17F 141.1 . . ? H17D C17 H17F 109.5 . . ? H17E C17 H17F 109.5 . . ? O1 C1 N1 122.5(2) . . ? O1 C1 C21 120.0(2) . . ? N1 C1 C21 117.50(17) . . ? C1 N1 C11 127.80(18) . . ? C1 N1 H1 113.0(16) . . ? C11 N1 H1 118.8(16) . . ? C12 C11 C16 117.8(2) . . ? C12 C11 N1 124.7(2) . . ? C16 C11 N1 117.47(19) . . ? C11 C12 C13 120.1(3) . . ? C11 C12 H12 120.0 . . ? C13 C12 H12 120.0 . . ? C14 C13 C12 121.3(3) . . ? C14 C13 H13 119.3 . . ? C12 C13 H13 119.3 . . ? C15 C14 F14 124.5(6) . . ? C15 C14 C13 119.0(3) . . ? F14 C14 C13 116.5(6) . . ? C15 C14 C17 118.8(6) . . ? C13 C14 C17 122.2(6) . . ? C14 C15 C16 120.7(3) . . ? C14 C15 H15 119.7 . . ? C16 C15 H15 119.7 . . ? C15 C16 C11 121.1(2) . . ? C15 C16 H16 119.5 . . ? C11 C16 H16 119.5 . . ? C26 C21 C22 116.7(2) . . ? C26 C21 C1 118.65(18) . . ? C22 C21 C1 124.62(19) . . ? N23 C22 C21 124.6(2) . . ? N23 C22 H22 117.7 . . ? C21 C22 H22 117.7 . . ? C22 N23 C24 117.02(18) . . ? N23 C24 C25 122.9(2) . . ? N23 C24 H24 118.5 . . ? C25 C24 H24 118.5 . . ? C26 C25 C24 119.0(2) . . ? C26 C25 H25 120.5 . . ? C24 C25 H25 120.5 . . ? C25 C26 C21 119.7(2) . . ? C25 C26 H26 120.1 . . ? C21 C26 H26 120.1 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 N1 C11 -0.7(4) . . . . ? C21 C1 N1 C11 -179.54(19) . . . . ? C1 N1 C11 C12 4.0(4) . . . . ? C1 N1 C11 C16 -177.0(2) . . . . ? C16 C11 C12 C13 0.8(4) . . . . ? N1 C11 C12 C13 179.8(2) . . . . ? C11 C12 C13 C14 0.0(4) . . . . ? C12 C13 C14 C15 -1.0(4) . . . . ? C12 C13 C14 F14 -179.2(6) . . . . ? C12 C13 C14 C17 179.7(8) . . . . ? F14 C14 C15 C16 179.1(7) . . . . ? C13 C14 C15 C16 1.1(4) . . . . ? C17 C14 C15 C16 -179.6(8) . . . . ? C14 C15 C16 C11 -0.2(4) . . . . ? C12 C11 C16 C15 -0.7(4) . . . . ? N1 C11 C16 C15 -179.8(2) . . . . ? O1 C1 C21 C26 1.7(3) . . . . ? N1 C1 C21 C26 -179.4(2) . . . . ? O1 C1 C21 C22 -177.7(2) . . . . ? N1 C1 C21 C22 1.1(3) . . . . ? C26 C21 C22 N23 -0.8(3) . . . . ? C1 C21 C22 N23 178.6(2) . . . . ? C21 C22 N23 C24 0.4(4) . . . . ? C22 N23 C24 C25 0.7(4) . . . . ? N23 C24 C25 C26 -1.4(5) . . . . ? C24 C25 C26 C21 1.0(4) . . . . ? C22 C21 C26 C25 0.0(4) . . . . ? C1 C21 C26 C25 -179.4(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag # # Hydrogen bonding scheme # ======== ======= ====== # # D H A D-H H...A D...A D-H...A symm publ # - - - --- ----- ----- ------- ---- ---- N1 H1 N23 0.92(3) 2.34(2) 3.207(2) 157(3) 2_564 yes C16 H16 N23 0.93 2.62 3.438(3) 147 2_564 yes C22 H22 N23 0.93 2.41 3.337(3) 178 2_564 yes C12 H12 O1 0.93 2.24 2.835(4) 122 . yes C26 H26 O1 0.93 2.58 3.194(2) 124 2 yes # C24 H24 F14 0.93 2.93 3.677(11) 139 3_457 yes # Weak interactions and contacts are included e.g. C24-H24...F14_3_457 #====================================================================== # END of details for NmpFM - the mixed 0.5:0.5 mixture of NmpF and NmpM #======================================================================