# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_5-hydroxyquinoline _database_code_depnum_ccdc_archive 'CCDC 908102' #TrackingRef '14997_web_deposit_cif_file_0_ArijitMukherjee_1351444746.5HQ.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H7 N O' _chemical_formula_weight 145.16 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 3.8348(9) _cell_length_b 12.718(3) _cell_length_c 14.067(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 686.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 6611 _cell_measurement_theta_min 3.2 _cell_measurement_theta_max 27.7 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.405 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 304 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.784 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ; XtaLABmini: Fixed Chi 2 circle ; _diffrn_measurement_device_type ; Rigaku Mercury375R (2x2 bin mode) ; _diffrn_detector_area_resol_mean 13.6612 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7008 _diffrn_reflns_av_R_equivalents 0.0327 _diffrn_reflns_av_sigmaI/netI 0.0248 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.20 _diffrn_reflns_theta_max 27.48 _reflns_number_total 1559 _reflns_number_gt 1444 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009) ; _computing_structure_solution 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0523P)^2^+0.0997P] 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 1559 _refine_ls_number_parameters 104 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0390 _refine_ls_R_factor_gt 0.0354 _refine_ls_wR_factor_ref 0.0908 _refine_ls_wR_factor_gt 0.0890 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group H1O H 0.229(6) 0.5116(17) 0.1430(15) 0.053(6) Uiso 1 1 d . . . C1 C 0.0239(4) 0.33399(11) -0.23140(10) 0.0224(3) Uani 1 1 d . . . H1 H -0.0252 0.2948 -0.2856 0.027 Uiso 1 1 calc R . . C2 C -0.0666(4) 0.29048(11) -0.14248(10) 0.0218(3) Uani 1 1 d . . . H2 H -0.1679 0.2242 -0.1383 0.026 Uiso 1 1 calc R . . C3 C -0.0013(4) 0.34836(11) -0.06264(9) 0.0191(3) Uani 1 1 d . . . H3 H -0.0650 0.3227 -0.0032 0.023 Uiso 1 1 calc R . . C4 C 0.1630(4) 0.44714(10) -0.07057(9) 0.0170(3) Uani 1 1 d . . . C5 C 0.2495(4) 0.48468(10) -0.16282(9) 0.0176(3) Uani 1 1 d . . . C6 C 0.4175(4) 0.58321(11) -0.17334(10) 0.0211(3) Uani 1 1 d . . . H6 H 0.4736 0.6085 -0.2334 0.025 Uiso 1 1 calc R . . C7 C 0.4958(4) 0.64059(11) -0.09410(10) 0.0221(3) Uani 1 1 d . . . H7 H 0.6048 0.7054 -0.1012 0.027 Uiso 1 1 calc R . . C8 C 0.4162(4) 0.60434(11) -0.00193(10) 0.0209(3) Uani 1 1 d . . . H8 H 0.4762 0.6447 0.0507 0.025 Uiso 1 1 calc R . . C9 C 0.2500(4) 0.50952(11) 0.01035(9) 0.0182(3) Uani 1 1 d . . . N1 N 0.1735(3) 0.42646(9) -0.24268(8) 0.0201(3) Uani 1 1 d . . . O1 O 0.1627(3) 0.46851(8) 0.09566(7) 0.0253(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0285(8) 0.0226(7) 0.0160(6) -0.0040(6) -0.0004(6) -0.0010(6) C2 0.0256(8) 0.0189(7) 0.0207(7) -0.0006(5) 0.0003(6) -0.0030(6) C3 0.0224(7) 0.0192(7) 0.0158(6) 0.0026(5) 0.0007(5) 0.0008(6) C4 0.0178(7) 0.0175(6) 0.0157(6) 0.0006(5) 0.0003(5) 0.0029(5) C5 0.0179(6) 0.0205(7) 0.0143(6) 0.0005(5) -0.0009(5) 0.0020(6) C6 0.0243(8) 0.0224(7) 0.0166(6) 0.0043(5) 0.0018(6) 0.0004(6) C7 0.0230(7) 0.0190(7) 0.0243(7) 0.0019(5) 0.0001(6) -0.0025(6) C8 0.0249(8) 0.0199(7) 0.0180(7) -0.0041(6) -0.0013(6) 0.0007(6) C9 0.0192(7) 0.0218(6) 0.0138(6) 0.0018(5) -0.0002(5) 0.0032(6) N1 0.0238(7) 0.0227(6) 0.0139(5) -0.0001(4) 0.0004(5) 0.0005(5) O1 0.0391(7) 0.0248(5) 0.0120(5) -0.0003(4) 0.0009(5) -0.0056(5) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.3181(18) . ? C1 C2 1.4111(19) . ? C2 C3 1.3660(18) . ? C3 C4 1.4098(18) . ? C4 C5 1.4220(17) . ? C4 C9 1.4270(18) . ? C5 N1 1.3767(17) . ? C5 C6 1.4166(19) . ? C6 C7 1.366(2) . ? C7 C8 1.4095(19) . ? C8 C9 1.375(2) . ? C9 O1 1.3506(16) . ? 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 N1 C1 C2 124.31(12) . . ? C3 C2 C1 118.19(13) . . ? C2 C3 C4 119.81(12) . . ? C3 C4 C5 118.41(12) . . ? C3 C4 C9 122.47(12) . . ? C5 C4 C9 119.12(12) . . ? N1 C5 C6 119.13(12) . . ? N1 C5 C4 120.97(12) . . ? C6 C5 C4 119.90(12) . . ? C7 C6 C5 119.17(12) . . ? C6 C7 C8 121.89(13) . . ? C9 C8 C7 120.19(12) . . ? O1 C9 C8 124.42(12) . . ? O1 C9 C4 115.85(12) . . ? C8 C9 C4 119.72(12) . . ? C1 N1 C5 118.29(11) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.187 _refine_diff_density_min -0.266 _refine_diff_density_rms 0.041 data_datam _database_code_depnum_ccdc_archive 'CCDC 908103' #TrackingRef '14998_web_deposit_cif_file_1_ArijitMukherjee_1351444746.4HBA_QUIN.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H18 N2 O6' _chemical_formula_weight 406.38 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.9109(14) _cell_length_b 12.289(3) _cell_length_c 12.647(3) _cell_angle_alpha 112.713(8) _cell_angle_beta 93.424(7) _cell_angle_gamma 103.103(7) _cell_volume 951.9(4) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 8832 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 27.6 _exptl_crystal_description needle _exptl_crystal_colour red _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.418 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 424 _exptl_absorpt_coefficient_mu 0.105 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.795 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ; XtaLABmini: Fixed Chi 2 circle ; _diffrn_measurement_device_type ; Rigaku Mercury375R (2x2 bin mode) ; _diffrn_detector_area_resol_mean 13.6612 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8123 _diffrn_reflns_av_R_equivalents 0.0304 _diffrn_reflns_av_sigmaI/netI 0.0373 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.06 _diffrn_reflns_theta_max 25.20 _reflns_number_total 3426 _reflns_number_gt 3002 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009) ; _computing_structure_solution 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0437P)^2^+1.7517P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3426 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0677 _refine_ls_R_factor_gt 0.0603 _refine_ls_wR_factor_ref 0.1647 _refine_ls_wR_factor_gt 0.1615 _refine_ls_goodness_of_fit_ref 1.214 _refine_ls_restrained_S_all 1.214 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.2649(3) 0.56246(19) 0.02302(17) 0.0244(5) Uani 1 1 d . . . H1O H 0.2599 0.5001 -0.0419 0.037 Uiso 1 1 d R . . O2 O 0.2559(3) 0.42889(18) 0.10276(17) 0.0225(5) Uani 1 1 d . . . O3 O 0.2657(4) 0.90946(19) 0.54516(18) 0.0307(6) Uani 1 1 d . . . H3O H 0.2540 0.9790 0.5430 0.046 Uiso 1 1 d R . . C9 C 0.2576(4) 0.5324(3) 0.1124(2) 0.0178(6) Uani 1 1 d . . . C10 C 0.2542(4) 0.6336(3) 0.2241(2) 0.0182(6) Uani 1 1 d . . . C11 C 0.2627(4) 0.7512(3) 0.2325(2) 0.0199(6) Uani 1 1 d . . . H11 H 0.2665 0.7668 0.1661 0.024 Uiso 1 1 calc R . . C12 C 0.2654(4) 0.8454(3) 0.3386(3) 0.0206(6) Uani 1 1 d . . . H12 H 0.2711 0.9235 0.3432 0.025 Uiso 1 1 calc R . . C13 C 0.2595(4) 0.8226(3) 0.4377(2) 0.0209(6) Uani 1 1 d . . . C14 C 0.2491(4) 0.7052(3) 0.4302(3) 0.0214(6) Uani 1 1 d . . . H14 H 0.2442 0.6896 0.4965 0.026 Uiso 1 1 calc R . . C15 C 0.2462(4) 0.6119(3) 0.3242(2) 0.0198(6) Uani 1 1 d . . . H15 H 0.2388 0.5337 0.3196 0.024 Uiso 1 1 calc R . . O4 O 0.8177(3) 0.97625(19) 0.87382(19) 0.0265(5) Uani 1 1 d . . . H4O H 0.9439 1.0129 0.9140 0.040 Uiso 1 1 d R . . O5 O 0.8063(3) 0.91203(19) 1.01726(18) 0.0261(5) Uani 1 1 d . . . O6 O -0.1124(3) 0.70725(18) 0.77990(17) 0.0232(5) Uani 1 1 d . . . H6O H -0.1580 0.6720 0.8250 0.035 Uiso 1 1 d R . . C16 C 0.7215(5) 0.9169(3) 0.9314(3) 0.0211(6) Uani 1 1 d . . . C17 C 0.5038(4) 0.8598(3) 0.8870(2) 0.0208(6) Uani 1 1 d . . . C18 C 0.4048(5) 0.8656(3) 0.7910(3) 0.0241(7) Uani 1 1 d . . . H18 H 0.4780 0.9045 0.7500 0.029 Uiso 1 1 calc R . . C19 C 0.1996(5) 0.8147(3) 0.7558(3) 0.0233(7) Uani 1 1 d . . . H19 H 0.1352 0.8194 0.6916 0.028 Uiso 1 1 calc R . . C20 C 0.0893(4) 0.7560(3) 0.8172(2) 0.0200(6) Uani 1 1 d . . . C21 C 0.1874(5) 0.7494(3) 0.9129(3) 0.0218(6) Uani 1 1 d . . . H21 H 0.1146 0.7105 0.9539 0.026 Uiso 1 1 calc R . . C22 C 0.3924(5) 0.8004(3) 0.9470(3) 0.0223(6) Uani 1 1 d . . . H22 H 0.4570 0.7952 1.0108 0.027 Uiso 1 1 calc R . . N1 N 0.2565(3) 0.3632(2) -0.1736(2) 0.0186(5) Uani 1 1 d . . . N2 N 0.2222(4) 0.1413(2) -0.3672(2) 0.0221(6) Uani 1 1 d . . . C1 C 0.2360(4) 0.2586(3) -0.1639(3) 0.0204(6) Uani 1 1 d . . . H1 H 0.2313 0.2573 -0.0911 0.024 Uiso 1 1 calc R . . C2 C 0.2207(4) 0.1482(3) -0.2611(3) 0.0223(6) Uani 1 1 d . . . H2 H 0.2091 0.0770 -0.2493 0.027 Uiso 1 1 calc R . . C3 C 0.2408(4) 0.2483(3) -0.3806(2) 0.0198(6) Uani 1 1 d . . . C4 C 0.2609(4) 0.3602(3) -0.2825(2) 0.0192(6) Uani 1 1 d . . . C5 C 0.2871(5) 0.4702(3) -0.2984(3) 0.0251(7) Uani 1 1 d . . . H5 H 0.3029 0.5443 -0.2349 0.030 Uiso 1 1 calc R . . C6 C 0.2888(5) 0.4668(3) -0.4070(3) 0.0326(8) Uani 1 1 d . . . H6 H 0.3061 0.5392 -0.4172 0.039 Uiso 1 1 calc R . . C7 C 0.2648(5) 0.3553(3) -0.5049(3) 0.0325(8) Uani 1 1 d . . . H7 H 0.2649 0.3549 -0.5786 0.039 Uiso 1 1 calc R . . C8 C 0.2416(5) 0.2484(3) -0.4918(3) 0.0267(7) Uani 1 1 d . . . H8 H 0.2262 0.1753 -0.5564 0.032 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 0.0389(13) 0.0219(11) 0.0138(10) 0.0074(8) 0.0062(9) 0.0103(9) O2 0.0308(12) 0.0171(10) 0.0196(11) 0.0069(8) 0.0067(9) 0.0068(9) O3 0.0533(15) 0.0207(11) 0.0192(12) 0.0060(9) 0.0095(10) 0.0150(10) C9 0.0149(14) 0.0213(15) 0.0168(15) 0.0078(12) 0.0024(11) 0.0039(11) C10 0.0153(14) 0.0203(14) 0.0176(15) 0.0065(12) 0.0029(11) 0.0045(11) C11 0.0211(15) 0.0228(15) 0.0172(15) 0.0104(12) 0.0045(11) 0.0045(12) C12 0.0212(15) 0.0181(14) 0.0242(16) 0.0100(12) 0.0049(12) 0.0063(12) C13 0.0202(15) 0.0195(14) 0.0190(15) 0.0034(12) 0.0042(11) 0.0059(12) C14 0.0266(16) 0.0246(15) 0.0170(15) 0.0103(12) 0.0059(12) 0.0105(12) C15 0.0214(15) 0.0174(14) 0.0220(15) 0.0084(12) 0.0044(12) 0.0072(11) O4 0.0245(11) 0.0287(12) 0.0289(12) 0.0163(10) 0.0053(9) 0.0038(9) O5 0.0248(11) 0.0293(12) 0.0254(12) 0.0148(9) 0.0026(9) 0.0036(9) O6 0.0242(11) 0.0254(11) 0.0192(11) 0.0117(9) -0.0002(8) 0.0017(9) C16 0.0262(16) 0.0166(14) 0.0217(16) 0.0082(12) 0.0072(12) 0.0068(12) C17 0.0254(16) 0.0159(14) 0.0200(15) 0.0059(11) 0.0053(12) 0.0056(12) C18 0.0298(17) 0.0240(15) 0.0205(16) 0.0119(13) 0.0063(13) 0.0055(13) C19 0.0296(17) 0.0241(15) 0.0178(15) 0.0109(12) 0.0019(12) 0.0063(13) C20 0.0243(15) 0.0150(13) 0.0171(15) 0.0035(11) 0.0027(11) 0.0045(11) C21 0.0274(16) 0.0200(15) 0.0195(15) 0.0107(12) 0.0045(12) 0.0042(12) C22 0.0274(16) 0.0221(15) 0.0195(15) 0.0112(12) 0.0019(12) 0.0065(12) N1 0.0172(12) 0.0203(12) 0.0175(13) 0.0066(10) 0.0019(9) 0.0060(10) N2 0.0216(13) 0.0225(13) 0.0207(13) 0.0061(10) 0.0026(10) 0.0081(10) C1 0.0217(15) 0.0251(15) 0.0163(15) 0.0096(12) 0.0040(11) 0.0077(12) C2 0.0234(15) 0.0206(15) 0.0254(17) 0.0104(12) 0.0047(12) 0.0091(12) C3 0.0144(14) 0.0237(15) 0.0182(15) 0.0061(12) 0.0011(11) 0.0046(11) C4 0.0145(14) 0.0230(15) 0.0206(15) 0.0087(12) 0.0020(11) 0.0065(11) C5 0.0272(16) 0.0222(15) 0.0255(17) 0.0096(13) 0.0026(13) 0.0071(13) C6 0.0338(19) 0.0352(19) 0.037(2) 0.0243(16) 0.0033(15) 0.0078(15) C7 0.0306(18) 0.049(2) 0.0214(17) 0.0211(16) 0.0013(13) 0.0065(15) C8 0.0239(16) 0.0346(18) 0.0176(16) 0.0075(13) 0.0026(12) 0.0064(13) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C9 1.319(3) . ? O1 H1O 0.8731 . ? O2 C9 1.227(3) . ? O3 C13 1.357(3) . ? O3 H3O 0.8865 . ? C9 C10 1.484(4) . ? C10 C15 1.392(4) . ? C10 C11 1.395(4) . ? C11 C12 1.389(4) . ? C11 H11 0.9300 . ? C12 C13 1.387(4) . ? C12 H12 0.9300 . ? C13 C14 1.393(4) . ? C14 C15 1.383(4) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? O4 C16 1.324(4) . ? O4 H4O 0.9021 . ? O5 C16 1.231(4) . ? O6 C20 1.360(4) . ? O6 H6O 0.8728 . ? C16 C17 1.479(4) . ? C17 C18 1.392(4) . ? C17 C22 1.395(4) . ? C18 C19 1.381(4) . ? C18 H18 0.9300 . ? C19 C20 1.400(4) . ? C19 H19 0.9300 . ? C20 C21 1.391(4) . ? C21 C22 1.379(4) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? N1 C1 1.315(4) . ? N1 C4 1.366(4) . ? N2 C2 1.312(4) . ? N2 C3 1.369(4) . ? C1 C2 1.413(4) . ? C1 H1 0.9300 . ? C2 H2 0.9300 . ? C3 C8 1.406(4) . ? C3 C4 1.423(4) . ? C4 C5 1.415(4) . ? C5 C6 1.359(5) . ? C5 H5 0.9300 . ? C6 C7 1.415(5) . ? C6 H6 0.9300 . ? C7 C8 1.362(5) . ? C7 H7 0.9300 . ? C8 H8 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 C9 O1 H1O 112.4 . . ? C13 O3 H3O 112.1 . . ? O2 C9 O1 121.9(3) . . ? O2 C9 C10 123.5(3) . . ? O1 C9 C10 114.6(2) . . ? C15 C10 C11 118.7(3) . . ? C15 C10 C9 119.4(3) . . ? C11 C10 C9 121.9(3) . . ? C12 C11 C10 120.9(3) . . ? C12 C11 H11 119.6 . . ? C10 C11 H11 119.6 . . ? C13 C12 C11 119.7(3) . . ? C13 C12 H12 120.1 . . ? C11 C12 H12 120.1 . . ? O3 C13 C12 123.7(3) . . ? O3 C13 C14 116.3(3) . . ? C12 C13 C14 119.9(3) . . ? C15 C14 C13 120.0(3) . . ? C15 C14 H14 120.0 . . ? C13 C14 H14 120.0 . . ? C14 C15 C10 120.8(3) . . ? C14 C15 H15 119.6 . . ? C10 C15 H15 119.6 . . ? C16 O4 H4O 106.0 . . ? C20 O6 H6O 106.7 . . ? O5 C16 O4 122.4(3) . . ? O5 C16 C17 122.5(3) . . ? O4 C16 C17 115.1(3) . . ? C18 C17 C22 118.8(3) . . ? C18 C17 C16 123.3(3) . . ? C22 C17 C16 117.8(3) . . ? C19 C18 C17 121.0(3) . . ? C19 C18 H18 119.5 . . ? C17 C18 H18 119.5 . . ? C18 C19 C20 119.6(3) . . ? C18 C19 H19 120.2 . . ? C20 C19 H19 120.2 . . ? O6 C20 C21 122.5(3) . . ? O6 C20 C19 117.8(3) . . ? C21 C20 C19 119.7(3) . . ? C22 C21 C20 120.1(3) . . ? C22 C21 H21 119.9 . . ? C20 C21 H21 119.9 . . ? C21 C22 C17 120.7(3) . . ? C21 C22 H22 119.6 . . ? C17 C22 H22 119.6 . . ? C1 N1 C4 116.9(2) . . ? C2 N2 C3 116.6(2) . . ? N1 C1 C2 121.8(3) . . ? N1 C1 H1 119.1 . . ? C2 C1 H1 119.1 . . ? N2 C2 C1 123.1(3) . . ? N2 C2 H2 118.4 . . ? C1 C2 H2 118.4 . . ? N2 C3 C8 120.1(3) . . ? N2 C3 C4 120.4(3) . . ? C8 C3 C4 119.5(3) . . ? N1 C4 C5 119.6(3) . . ? N1 C4 C3 121.1(3) . . ? C5 C4 C3 119.2(3) . . ? C6 C5 C4 119.5(3) . . ? C6 C5 H5 120.2 . . ? C4 C5 H5 120.2 . . ? C5 C6 C7 121.3(3) . . ? C5 C6 H6 119.3 . . ? C7 C6 H6 119.3 . . ? C8 C7 C6 120.3(3) . . ? C8 C7 H7 119.9 . . ? C6 C7 H7 119.9 . . ? C7 C8 C3 120.1(3) . . ? C7 C8 H8 119.9 . . ? C3 C8 H8 119.9 . . ? 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 O2 C9 C10 C15 -0.8(4) . . . . ? O1 C9 C10 C15 179.9(3) . . . . ? O2 C9 C10 C11 178.0(3) . . . . ? O1 C9 C10 C11 -1.3(4) . . . . ? C15 C10 C11 C12 0.7(4) . . . . ? C9 C10 C11 C12 -178.1(3) . . . . ? C10 C11 C12 C13 0.0(4) . . . . ? C11 C12 C13 O3 178.6(3) . . . . ? C11 C12 C13 C14 -0.6(4) . . . . ? O3 C13 C14 C15 -178.8(3) . . . . ? C12 C13 C14 C15 0.5(4) . . . . ? C13 C14 C15 C10 0.2(4) . . . . ? C11 C10 C15 C14 -0.8(4) . . . . ? C9 C10 C15 C14 178.0(3) . . . . ? O5 C16 C17 C18 179.2(3) . . . . ? O4 C16 C17 C18 0.7(4) . . . . ? O5 C16 C17 C22 1.2(4) . . . . ? O4 C16 C17 C22 -177.3(3) . . . . ? C22 C17 C18 C19 0.5(4) . . . . ? C16 C17 C18 C19 -177.4(3) . . . . ? C17 C18 C19 C20 -0.2(4) . . . . ? C18 C19 C20 O6 179.9(3) . . . . ? C18 C19 C20 C21 -0.1(4) . . . . ? O6 C20 C21 C22 180.0(3) . . . . ? C19 C20 C21 C22 0.0(4) . . . . ? C20 C21 C22 C17 0.4(4) . . . . ? C18 C17 C22 C21 -0.6(4) . . . . ? C16 C17 C22 C21 177.4(3) . . . . ? C4 N1 C1 C2 0.5(4) . . . . ? C3 N2 C2 C1 0.4(4) . . . . ? N1 C1 C2 N2 -1.3(5) . . . . ? C2 N2 C3 C8 -179.4(3) . . . . ? C2 N2 C3 C4 1.0(4) . . . . ? C1 N1 C4 C5 -178.6(3) . . . . ? C1 N1 C4 C3 1.0(4) . . . . ? N2 C3 C4 N1 -1.8(4) . . . . ? C8 C3 C4 N1 178.6(3) . . . . ? N2 C3 C4 C5 177.8(3) . . . . ? C8 C3 C4 C5 -1.8(4) . . . . ? N1 C4 C5 C6 -179.2(3) . . . . ? C3 C4 C5 C6 1.2(4) . . . . ? C4 C5 C6 C7 0.0(5) . . . . ? C5 C6 C7 C8 -0.8(5) . . . . ? C6 C7 C8 C3 0.2(5) . . . . ? N2 C3 C8 C7 -178.5(3) . . . . ? C4 C3 C8 C7 1.1(4) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.20 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.293 _refine_diff_density_min -0.256 _refine_diff_density_rms 0.060 data_datam2 _database_code_depnum_ccdc_archive 'CCDC 908104' #TrackingRef '14999_web_deposit_cif_file_2_ArijitMukherjee_1351444746.4HBA_DPE.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H22 N2 O6' _chemical_formula_weight 458.46 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' _symmetry_cell_setting ? _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 3.9080(6) _cell_length_b 23.780(4) _cell_length_c 11.839(2) _cell_angle_alpha 90.00 _cell_angle_beta 100.833(9) _cell_angle_gamma 90.00 _cell_volume 1080.6(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3014 _cell_measurement_theta_min 1.9 _cell_measurement_theta_max 27.5 _exptl_crystal_description plate _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.409 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 480 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.809 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11126 _diffrn_reflns_av_R_equivalents 0.1370 _diffrn_reflns_av_sigmaI/netI 0.0751 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.71 _diffrn_reflns_theta_max 27.52 _reflns_number_total 2461 _reflns_number_gt 2239 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009) ; _computing_structure_solution 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0518P)^2^+0.2734P] 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 2461 _refine_ls_number_parameters 166 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0524 _refine_ls_R_factor_gt 0.0482 _refine_ls_wR_factor_ref 0.1360 _refine_ls_wR_factor_gt 0.1259 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.0348(3) -0.01723(6) -0.67469(12) 0.0255(3) Uani 1 1 d . . . H1 H 0.1688 0.0090 -0.6275 0.031 Uiso 1 1 calc R . . C2 C -0.1232(3) -0.00105(5) -0.78419(11) 0.0232(3) Uani 1 1 d . . . H2 H -0.0940 0.0354 -0.8094 0.028 Uiso 1 1 calc R . . C3 C -0.3268(3) -0.03942(5) -0.85710(11) 0.0209(3) Uani 1 1 d . . . C4 C -0.3578(3) -0.09367(5) -0.81406(11) 0.0236(3) Uani 1 1 d . . . H4 H -0.4888 -0.1208 -0.8595 0.028 Uiso 1 1 calc R . . C5 C -0.1909(4) -0.10661(6) -0.70267(12) 0.0262(3) Uani 1 1 d . . . H5 H -0.2147 -0.1427 -0.6749 0.031 Uiso 1 1 calc R . . C6 C -0.5061(3) -0.02498(6) -0.97449(11) 0.0224(3) Uani 1 1 d . . . C7 C -0.5175(3) -0.14666(5) -0.42408(11) 0.0216(3) Uani 1 1 d . . . C8 C -0.3187(3) -0.16371(5) -0.31025(10) 0.0192(3) Uani 1 1 d . . . C9 C -0.1416(3) -0.21516(5) -0.29879(11) 0.0214(3) Uani 1 1 d . . . H9 H -0.1480 -0.2380 -0.3629 0.026 Uiso 1 1 calc R . . C10 C 0.0431(3) -0.23241(5) -0.19295(11) 0.0217(3) Uani 1 1 d . . . H10 H 0.1623 -0.2665 -0.1864 0.026 Uiso 1 1 calc R . . C11 C 0.0501(3) -0.19858(5) -0.09605(11) 0.0205(3) Uani 1 1 d . . . C12 C -0.1300(3) -0.14765(5) -0.10627(11) 0.0217(3) Uani 1 1 d . . . H12 H -0.1283 -0.1253 -0.0418 0.026 Uiso 1 1 calc R . . C13 C -0.3117(3) -0.13046(5) -0.21260(11) 0.0211(3) Uani 1 1 d . . . H13 H -0.4303 -0.0964 -0.2190 0.025 Uiso 1 1 calc R . . N1 N 0.0027(3) -0.06925(5) -0.63359(10) 0.0264(3) Uani 1 1 d . . . O1 O 0.2302(3) -0.21296(4) 0.00972(8) 0.0268(3) Uani 1 1 d . . . O2 O -0.5750(3) -0.17885(4) -0.50716(8) 0.0306(3) Uani 1 1 d . . . O3 O -0.6296(3) -0.09435(4) -0.43049(9) 0.0290(3) Uani 1 1 d . . . H1O H 0.327(5) -0.2483(10) 0.0066(18) 0.050(6) Uiso 1 1 d . . . H3O H -0.784(7) -0.0878(11) -0.511(2) 0.079(8) Uiso 1 1 d . . . H26 H -0.657(5) -0.0548(8) -1.0160(16) 0.038(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0274(6) 0.0238(6) 0.0235(6) 0.0000(5) 0.0001(5) 0.0028(5) C2 0.0257(6) 0.0188(6) 0.0244(6) 0.0024(5) 0.0028(5) 0.0022(5) C3 0.0209(6) 0.0210(6) 0.0207(6) 0.0026(5) 0.0038(5) 0.0034(5) C4 0.0266(7) 0.0208(6) 0.0224(6) 0.0012(5) 0.0023(5) -0.0004(5) C5 0.0313(7) 0.0224(6) 0.0245(7) 0.0052(5) 0.0044(5) 0.0021(5) C6 0.0231(6) 0.0226(6) 0.0204(6) 0.0021(5) 0.0008(5) 0.0011(5) C7 0.0246(6) 0.0196(6) 0.0197(6) 0.0013(5) 0.0019(5) -0.0032(5) C8 0.0209(6) 0.0183(6) 0.0179(6) 0.0003(5) 0.0023(5) -0.0030(4) C9 0.0262(6) 0.0194(6) 0.0187(6) -0.0018(5) 0.0042(5) -0.0018(5) C10 0.0237(6) 0.0179(6) 0.0228(6) 0.0002(5) 0.0028(5) 0.0010(4) C11 0.0220(6) 0.0213(6) 0.0175(6) 0.0028(5) 0.0020(5) -0.0039(4) C12 0.0268(6) 0.0203(6) 0.0183(6) -0.0014(5) 0.0047(5) -0.0017(5) C13 0.0231(6) 0.0179(6) 0.0219(6) -0.0001(5) 0.0030(5) -0.0005(4) N1 0.0295(6) 0.0259(6) 0.0223(6) 0.0037(5) 0.0013(5) 0.0049(4) O1 0.0349(6) 0.0249(5) 0.0180(5) 0.0034(4) -0.0016(4) 0.0014(4) O2 0.0456(6) 0.0231(5) 0.0198(5) -0.0018(4) -0.0027(4) -0.0022(4) O3 0.0394(6) 0.0208(5) 0.0232(5) 0.0014(4) -0.0034(4) 0.0039(4) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.3437(18) . ? C1 C2 1.3816(18) . ? C1 H1 0.9300 . ? C2 C3 1.3973(18) . ? C2 H2 0.9300 . ? C3 C4 1.4007(18) . ? C3 C6 1.4747(17) . ? C4 C5 1.3913(19) . ? C4 H4 0.9300 . ? C5 N1 1.3411(18) . ? C5 H5 0.9300 . ? C6 C6 1.338(3) 3_453 ? C6 H26 0.99(2) . ? C7 O2 1.2332(16) . ? C7 O3 1.3164(16) . ? C7 C8 1.4800(17) . ? C8 C13 1.3967(18) . ? C8 C9 1.3996(18) . ? C9 C10 1.3855(17) . ? C9 H9 0.9300 . ? C10 C11 1.3973(18) . ? C10 H10 0.9300 . ? C11 O1 1.3597(15) . ? C11 C12 1.3947(18) . ? C12 C13 1.3856(18) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? O1 H1O 0.93(2) . ? O3 H3O 1.04(3) . ? 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 N1 C1 C2 122.72(13) . . ? N1 C1 H1 118.6 . . ? C2 C1 H1 118.6 . . ? C1 C2 C3 120.00(12) . . ? C1 C2 H2 120.0 . . ? C3 C2 H2 120.0 . . ? C2 C3 C4 117.06(12) . . ? C2 C3 C6 123.01(12) . . ? C4 C3 C6 119.93(12) . . ? C5 C4 C3 119.43(13) . . ? C5 C4 H4 120.3 . . ? C3 C4 H4 120.3 . . ? N1 C5 C4 122.80(12) . . ? N1 C5 H5 118.6 . . ? C4 C5 H5 118.6 . . ? C6 C6 C3 125.54(16) 3_453 . ? C6 C6 H26 118.6(11) 3_453 . ? C3 C6 H26 115.7(11) . . ? O2 C7 O3 122.12(12) . . ? O2 C7 C8 122.82(12) . . ? O3 C7 C8 115.06(11) . . ? C13 C8 C9 118.83(12) . . ? C13 C8 C7 121.59(11) . . ? C9 C8 C7 119.55(11) . . ? C10 C9 C8 120.71(12) . . ? C10 C9 H9 119.6 . . ? C8 C9 H9 119.6 . . ? C9 C10 C11 119.90(12) . . ? C9 C10 H10 120.0 . . ? C11 C10 H10 120.0 . . ? O1 C11 C12 117.63(12) . . ? O1 C11 C10 122.56(12) . . ? C12 C11 C10 119.81(12) . . ? C13 C12 C11 119.94(12) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C12 C13 C8 120.79(12) . . ? C12 C13 H13 119.6 . . ? C8 C13 H13 119.6 . . ? C5 N1 C1 117.99(12) . . ? C11 O1 H1O 109.7(13) . . ? C7 O3 H3O 109.0(15) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 0.1(2) . . . . ? C1 C2 C3 C4 -0.45(18) . . . . ? C1 C2 C3 C6 179.32(12) . . . . ? C2 C3 C4 C5 0.57(18) . . . . ? C6 C3 C4 C5 -179.22(12) . . . . ? C3 C4 C5 N1 -0.4(2) . . . . ? C2 C3 C6 C6 0.9(2) . . . 3_453 ? C4 C3 C6 C6 -179.31(16) . . . 3_453 ? O2 C7 C8 C13 -167.92(13) . . . . ? O3 C7 C8 C13 12.04(17) . . . . ? O2 C7 C8 C9 10.09(19) . . . . ? O3 C7 C8 C9 -169.95(11) . . . . ? C13 C8 C9 C10 -1.20(19) . . . . ? C7 C8 C9 C10 -179.27(11) . . . . ? C8 C9 C10 C11 0.78(19) . . . . ? C9 C10 C11 O1 -179.19(11) . . . . ? C9 C10 C11 C12 0.22(19) . . . . ? O1 C11 C12 C13 178.66(11) . . . . ? C10 C11 C12 C13 -0.78(19) . . . . ? C11 C12 C13 C8 0.35(19) . . . . ? C9 C8 C13 C12 0.63(19) . . . . ? C7 C8 C13 C12 178.66(11) . . . . ? C4 C5 N1 C1 0.0(2) . . . . ? C2 C1 N1 C5 0.1(2) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.263 _refine_diff_density_min -0.262 _refine_diff_density_rms 0.058 data_platon _database_code_depnum_ccdc_archive 'CCDC 919101' #TrackingRef 'web_deposit_cif_file_0_SrinuTothadi_1357839835.2,6-Difluorobenzamide.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 2,6-Difluorobenzamide _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C7 H5 F2 N O' _chemical_formula_weight 157.08 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0030 0.0020 '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' F F 0.0170 0.0100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0110 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' 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 5.1396(15) _cell_length_b 12.118(4) _cell_length_c 11.792(3) _cell_angle_alpha 90.00 _cell_angle_beta 112.482(11) _cell_angle_gamma 90.00 _cell_volume 678.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 6286 _cell_measurement_theta_min 3.4 _cell_measurement_theta_max 27.6 _exptl_crystal_description block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.537 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 320 _exptl_absorpt_coefficient_mu 0.141 # Permitted for _exptl_absorpt_correction_type : # analytical 'analytical from crystal shape' # Example: de Meulenaer&Tompa: ABST # cylinder 'cylindrical' # gaussian 'Gaussian from crystal shape' # Example: PLATON/ABSG # integration 'integration from crystal shape' # multi-scan 'symmetry-related measurements' # Example: SADABS, MULABS # none 'no absorption corr. applied' # numerical 'numerical from crystal shape' # psi-scan 'psi-scan corrections' # Example: PLATON/ABSP # refdelf 'refined from delta-F' # Example: SHELXA, # sphere 'spherical' # Example: PLATON/ABSS _exptl_absorpt_correction_type Multi-scan # Example: '(North et al., 1968)' _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_absorpt_correction_T_min 0.9590 _exptl_absorpt_correction_T_max 0.9724 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ; XtaLABmini: Fixed Chi 2 circle ; _diffrn_measurement_device_type ; Rigaku Mercury375R (2x2 bin mode) ; _diffrn_measurement_method 'profile data from \w-scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6733 _diffrn_reflns_av_R_equivalents 0.0259 _diffrn_reflns_av_sigmaI/netI 0.0190 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.36 _diffrn_reflns_theta_max 27.48 _reflns_number_total 1555 _reflns_number_gt 1401 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009) ; _computing_structure_solution 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0450P)^2^+0.2355P] 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 1555 _refine_ls_number_parameters 108 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0393 _refine_ls_R_factor_gt 0.0355 _refine_ls_wR_factor_ref 0.0934 _refine_ls_wR_factor_gt 0.0909 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group F1 F 0.11960(15) 0.32911(6) 0.48428(8) 0.0336(2) Uani 1 1 d . . . F2 F 1.06680(16) 0.24640(7) 0.72517(8) 0.0359(2) Uani 1 1 d . . . O1 O 0.32616(18) 0.11590(7) 0.54063(9) 0.0258(2) Uani 1 1 d . . . N1 N 0.7390(2) 0.12252(9) 0.51612(11) 0.0263(3) Uani 1 1 d . . . C1 C 0.8456(3) 0.31708(10) 0.68862(11) 0.0245(3) Uani 1 1 d . . . C2 C 0.5913(2) 0.28106(9) 0.60152(11) 0.0201(3) Uani 1 1 d . . . C3 C 0.5431(2) 0.16581(9) 0.54995(11) 0.0196(2) Uani 1 1 d . . . C4 C 0.4026(3) 0.46234(10) 0.61861(13) 0.0296(3) Uani 1 1 d . . . H H 0.2487 0.5124 0.5934 0.036 Uiso 1 1 calc R . . C5 C 0.3736(3) 0.35766(10) 0.56948(12) 0.0237(3) Uani 1 1 d . . . C6 C 0.8865(3) 0.42018(11) 0.74169(12) 0.0311(3) Uani 1 1 d . . . H6 H 1.0643 0.4409 0.8015 0.037 Uiso 1 1 calc R . . C7 C 0.6618(3) 0.49268(11) 0.70560(13) 0.0318(3) Uani 1 1 d . . . H7 H 0.6856 0.5643 0.7410 0.038 Uiso 1 1 calc R . . H2 H 0.896(4) 0.1559(15) 0.5280(15) 0.041(5) Uiso 1 1 d . . . H1 H 0.714(3) 0.0525(15) 0.4925(14) 0.033(4) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F1 0.0224(4) 0.0252(4) 0.0462(5) -0.0030(3) 0.0054(3) 0.0037(3) F2 0.0250(4) 0.0343(5) 0.0393(5) -0.0038(3) 0.0022(3) 0.0059(3) O1 0.0221(4) 0.0184(4) 0.0413(5) -0.0043(4) 0.0170(4) -0.0027(3) N1 0.0227(5) 0.0186(5) 0.0430(7) -0.0073(5) 0.0187(5) -0.0030(4) C1 0.0237(6) 0.0239(6) 0.0261(6) -0.0001(5) 0.0099(5) 0.0012(5) C2 0.0234(6) 0.0161(5) 0.0246(6) -0.0002(4) 0.0133(5) -0.0012(4) C3 0.0197(5) 0.0164(5) 0.0235(6) 0.0008(4) 0.0091(4) 0.0009(4) C4 0.0351(7) 0.0182(6) 0.0406(7) 0.0000(5) 0.0203(6) 0.0034(5) C5 0.0223(6) 0.0200(6) 0.0298(6) -0.0005(5) 0.0113(5) -0.0010(4) C6 0.0334(7) 0.0301(7) 0.0288(7) -0.0084(5) 0.0108(5) -0.0081(5) C7 0.0449(8) 0.0200(6) 0.0370(7) -0.0080(5) 0.0228(6) -0.0069(5) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 F1 C5 1.3528(15) . ? F2 C1 1.3553(14) . ? O1 C3 1.2358(14) . ? N1 C3 1.3247(15) . ? N1 H2 0.866(18) . ? N1 H1 0.887(18) . ? C1 C6 1.3771(18) . ? C1 C2 1.3882(17) . ? C2 C5 1.3903(17) . ? C2 C3 1.5055(16) . ? C4 C5 1.3787(18) . ? C4 C7 1.385(2) . ? C4 H 0.9500 . ? C6 C7 1.382(2) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? 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 C3 N1 H2 122.4(12) . . ? C3 N1 H1 115.8(10) . . ? H2 N1 H1 120.9(16) . . ? F2 C1 C6 117.73(12) . . ? F2 C1 C2 118.33(11) . . ? C6 C1 C2 123.94(12) . . ? C1 C2 C5 115.05(11) . . ? C1 C2 C3 123.61(11) . . ? C5 C2 C3 121.23(11) . . ? O1 C3 N1 122.90(11) . . ? O1 C3 C2 119.57(10) . . ? N1 C3 C2 117.53(10) . . ? C5 C4 C7 118.33(12) . . ? C5 C4 H 120.8 . . ? C7 C4 H 120.8 . . ? F1 C5 C4 117.77(11) . . ? F1 C5 C2 118.61(11) . . ? C4 C5 C2 123.61(12) . . ? C1 C6 C7 118.20(12) . . ? C1 C6 H6 120.9 . . ? C7 C6 H6 120.9 . . ? C6 C7 C4 120.87(12) . . ? C6 C7 H7 119.6 . . ? C4 C7 H7 119.6 . . ? 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 F2 C1 C2 C5 179.40(11) . . . . ? C6 C1 C2 C5 0.28(18) . . . . ? F2 C1 C2 C3 3.23(18) . . . . ? C6 C1 C2 C3 -175.89(12) . . . . ? C1 C2 C3 O1 134.60(13) . . . . ? C5 C2 C3 O1 -41.35(16) . . . . ? C1 C2 C3 N1 -45.52(16) . . . . ? C5 C2 C3 N1 138.54(12) . . . . ? C7 C4 C5 F1 -179.79(11) . . . . ? C7 C4 C5 C2 -0.7(2) . . . . ? C1 C2 C5 F1 179.41(11) . . . . ? C3 C2 C5 F1 -4.31(17) . . . . ? C1 C2 C5 C4 0.35(18) . . . . ? C3 C2 C5 C4 176.62(12) . . . . ? F2 C1 C6 C7 -179.63(12) . . . . ? C2 C1 C6 C7 -0.5(2) . . . . ? C1 C6 C7 C4 0.1(2) . . . . ? C5 C4 C7 C6 0.5(2) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.334 _refine_diff_density_min -0.195 _refine_diff_density_rms 0.043