# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_030615 _database_code_depnum_ccdc_archive 'CCDC 805769' #TrackingRef '56MeO.cif' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C13 H16 N2 O4' _chemical_formula_moiety 'C13 H16 N2 O4' _chemical_formula_weight 264.28 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,1/2+Y,1/2-Z 3 -X,-Y,-Z 4 +X,1/2-Y,1/2+Z #------------------------------------------------------------------------------ _cell_length_a 7.138(3) _cell_length_b 21.173(9) _cell_length_c 8.531(4) _cell_angle_alpha 90.0000 _cell_angle_beta 98.715(7) _cell_angle_gamma 90.0000 _cell_volume 1274.4(9) _cell_formula_units_Z 4 _cell_measurement_reflns_used 3085 _cell_measurement_theta_min 3.09 _cell_measurement_theta_max 27.48 _cell_measurement_temperature 153 #------------------------------------------------------------------------------ _exptl_crystal_description platelet _exptl_crystal_colour colorless _exptl_crystal_size_max 0.130 _exptl_crystal_size_mid 0.130 _exptl_crystal_size_min 0.020 _exptl_crystal_density_diffrn 1.377 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 560.00 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'REQAB (Rigaku, 1998)' _exptl_absorpt_correction_T_min 0.900 _exptl_absorpt_correction_T_max 0.998 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 153 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71070 _diffrn_measurement_device_type 'Rigaku Mercury70' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 7.314 _diffrn_reflns_number 7691 _diffrn_reflns_av_R_equivalents 0.0455 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_max 0.977 _diffrn_measured_fraction_theta_full 0.977 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 10 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_decay_% ? #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 2854 _reflns_number_gt 2088 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0753 _refine_ls_wR_factor_ref 0.2018 _refine_ls_number_restraints ? _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 2854 _refine_ls_number_parameters 188 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[0.0043Fo^2^ + 1.0000\s(Fo^2^)]/(4Fo^2^)' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_diff_density_max 0.638 _refine_diff_density_min -0.692 _refine_ls_extinction_method none _refine_ls_extinction_coef ? 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 for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.0000 0.0000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; N N 0.0061 0.0033 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.0106 0.0060 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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 0.2402(3) 0.02511(8) 0.9839(2) 0.0184(5) Uani 1.0 4 d . . . O2 O 0.2559(3) -0.03592(9) 0.5144(2) 0.0217(5) Uani 1.0 4 d . . . O3 O 0.2349(3) 0.32883(8) 0.7006(3) 0.0267(6) Uani 1.0 4 d . . . O4 O 0.5342(3) 0.31237(8) 0.9042(3) 0.0233(6) Uani 1.0 4 d . . . N1 N -0.0052(3) 0.01814(10) 0.7864(3) 0.0190(6) Uani 1.0 4 d . . . N2 N 0.4705(3) -0.05645(10) 0.7316(3) 0.0194(6) Uani 1.0 4 d . . . C1 C 0.4892(4) 0.07803(11) 0.7984(3) 0.0152(7) Uani 1.0 4 d . . . C2 C 0.3071(4) 0.04469(11) 0.7169(3) 0.0132(7) Uani 1.0 4 d . . . C3 C 0.2171(4) 0.09360(11) 0.5933(3) 0.0151(7) Uani 1.0 4 d . . . C4 C 0.2771(4) 0.15547(11) 0.6733(3) 0.0156(7) Uani 1.0 4 d . . . C5 C 0.2044(4) 0.21599(12) 0.6401(4) 0.0187(7) Uani 1.0 4 d . . . C6 C 0.2928(4) 0.26716(12) 0.7223(4) 0.0192(7) Uani 1.0 4 d . . . C7 C 0.4553(4) 0.25781(12) 0.8360(4) 0.0184(7) Uani 1.0 4 d . . . C8 C 0.5233(4) 0.19757(12) 0.8711(3) 0.0178(7) Uani 1.0 4 d . . . C9 C 0.4329(4) 0.14675(11) 0.7892(3) 0.0159(7) Uani 1.0 4 d . . . C10 C 0.1763(4) 0.02950(11) 0.8404(3) 0.0136(6) Uani 1.0 4 d . . . C11 C 0.3444(4) -0.01942(11) 0.6437(3) 0.0135(7) Uani 1.0 4 d . . . C12 C 0.0665(5) 0.34011(14) 0.5929(5) 0.0342(9) Uani 1.0 4 d . . . C13 C 0.7156(4) 0.30637(13) 0.9990(4) 0.0266(8) Uani 1.0 4 d . . . H1 H -0.0867 0.0062 0.8564 0.0230 Uiso 1.0 4 calc R . . H2 H -0.0505 0.0220 0.6787 0.0227 Uiso 1.0 4 calc R . . H3 H 0.4954 -0.0967 0.6966 0.0227 Uiso 1.0 4 calc R . . H4 H 0.5333 -0.0418 0.8283 0.0229 Uiso 1.0 4 calc R . . H5 H 0.5238 0.0654 0.9083 0.0181 Uiso 1.0 4 calc R . . H6 H 0.5956 0.0710 0.7421 0.0181 Uiso 1.0 4 calc R . . H7 H 0.2667 0.0908 0.4938 0.0180 Uiso 1.0 4 calc R . . H8 H 0.0799 0.0912 0.5728 0.0179 Uiso 1.0 4 calc R . . H9 H 0.0981 0.2216 0.5637 0.0220 Uiso 1.0 4 calc R . . H10 H 0.6285 0.1912 0.9482 0.0209 Uiso 1.0 4 calc R . . H11 H -0.0386 0.3220 0.6326 0.0397 Uiso 1.0 4 calc R . . H13 H 0.0788 0.3214 0.4937 0.0397 Uiso 1.0 4 calc R . . H15 H 0.7463 0.3523 1.0361 0.0307 Uiso 1.0 4 calc R . . H14 H 0.8036 0.2900 0.9362 0.0307 Uiso 1.0 4 calc R . . H16 H 0.7068 0.2784 1.0846 0.0308 Uiso 1.0 4 calc R . . H12 H 0.0466 0.3843 0.5803 0.0398 Uiso 1.0 4 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 0.0172(10) 0.0260(11) 0.0119(10) -0.0008(8) 0.0011(8) 0.0022(8) O2 0.0276(11) 0.0193(10) 0.0162(10) 0.0018(8) -0.0031(8) -0.0043(8) O3 0.0245(11) 0.0122(9) 0.0398(13) 0.0015(8) -0.0066(10) 0.0028(9) O4 0.0184(10) 0.0142(10) 0.0346(12) -0.0025(8) -0.0042(9) -0.0025(8) N1 0.0149(12) 0.0285(13) 0.0134(11) -0.0020(9) 0.0018(9) 0.0038(9) N2 0.0220(12) 0.0165(11) 0.0180(12) 0.0034(9) -0.0025(10) -0.0034(9) C1 0.0126(13) 0.0155(12) 0.0170(13) -0.0006(10) 0.0004(10) 0.0005(11) C2 0.0159(13) 0.0107(12) 0.0125(13) 0.0013(10) 0.0003(10) 0.0015(10) C3 0.0159(13) 0.0151(12) 0.0137(13) 0.0003(10) -0.0001(10) 0.0019(10) C4 0.0145(13) 0.0143(13) 0.0176(14) -0.0021(10) 0.0010(11) 0.0019(10) C5 0.0163(14) 0.0166(13) 0.0225(15) -0.0018(10) 0.0001(11) 0.0046(11) C6 0.0162(13) 0.0125(13) 0.0294(16) 0.0003(10) 0.0047(11) 0.0035(11) C7 0.0176(14) 0.0155(13) 0.0220(15) -0.0044(11) 0.0027(11) -0.0022(11) C8 0.0136(13) 0.0191(13) 0.0199(14) 0.0008(10) -0.0003(11) 0.0015(11) C9 0.0145(13) 0.0137(12) 0.0196(14) 0.0028(10) 0.0032(11) 0.0037(10) C10 0.0159(13) 0.0095(11) 0.0148(13) 0.0005(10) 0.0005(10) -0.0005(10) C11 0.0118(12) 0.0127(12) 0.0161(14) -0.0006(10) 0.0024(10) 0.0019(10) C12 0.0285(17) 0.0180(14) 0.053(3) 0.0044(12) -0.0050(15) 0.0073(14) C13 0.0259(16) 0.0188(14) 0.0320(17) -0.0032(12) -0.0059(13) -0.0033(12) #============================================================================== _computing_data_collection 'CrystalClear (Rigaku Corp., 2000)' _computing_cell_refinement CrystalClear _computing_data_reduction CrystalClear _computing_structure_solution SIR97 _computing_structure_refinement 'CRYSTALS (Carruthers, et al., 1999)' _computing_publication_material 'CrystalStructure 4.0 (Rigaku, 2010)' _computing_molecular_graphics 'CrystalStructure 4.0' #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 O1 C10 1.243(3) yes . . O2 C11 1.236(3) yes . . O3 C6 1.374(3) yes . . O3 C12 1.418(4) yes . . O4 C7 1.375(3) yes . . O4 C13 1.425(4) yes . . N1 C10 1.329(4) yes . . N2 C11 1.335(3) yes . . C1 C2 1.548(4) yes . . C1 C9 1.508(4) yes . . C2 C3 1.547(4) yes . . C2 C10 1.544(4) yes . . C2 C11 1.534(4) yes . . C3 C4 1.509(4) yes . . C4 C5 1.395(4) yes . . C4 C9 1.384(4) yes . . C5 C6 1.389(4) yes . . C6 C7 1.409(4) yes . . C7 C8 1.381(4) yes . . C8 C9 1.387(4) yes . . N1 H1 0.930 no . . N1 H2 0.930 no . . N2 H3 0.930 no . . N2 H4 0.930 no . . C1 H5 0.970 no . . C1 H6 0.970 no . . C3 H7 0.970 no . . C3 H8 0.970 no . . C5 H9 0.930 no . . C8 H10 0.930 no . . C12 H11 0.950 no . . C12 H13 0.950 no . . C12 H12 0.950 no . . C13 H15 1.036 no . . C13 H14 0.950 no . . C13 H16 0.950 no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 C6 O3 C12 117.1(2) yes . . . C7 O4 C13 116.4(2) yes . . . C2 C1 C9 102.59(19) yes . . . C1 C2 C3 103.57(19) yes . . . C1 C2 C10 110.0(2) yes . . . C1 C2 C11 113.6(2) yes . . . C3 C2 C10 111.9(2) yes . . . C3 C2 C11 113.2(2) yes . . . C10 C2 C11 104.7(2) yes . . . C2 C3 C4 102.28(19) yes . . . C3 C4 C5 129.4(3) yes . . . C3 C4 C9 110.5(2) yes . . . C5 C4 C9 120.1(3) yes . . . C4 C5 C6 119.2(3) yes . . . O3 C6 C5 124.7(3) yes . . . O3 C6 C7 115.2(3) yes . . . C5 C6 C7 120.1(3) yes . . . O4 C7 C6 114.5(3) yes . . . O4 C7 C8 125.2(3) yes . . . C6 C7 C8 120.3(3) yes . . . C7 C8 C9 119.1(3) yes . . . C1 C9 C4 110.1(2) yes . . . C1 C9 C8 128.5(3) yes . . . C4 C9 C8 121.2(3) yes . . . O1 C10 N1 121.4(3) yes . . . O1 C10 C2 121.2(3) yes . . . N1 C10 C2 117.3(3) yes . . . O2 C11 N2 123.1(3) yes . . . O2 C11 C2 121.1(2) yes . . . N2 C11 C2 115.7(2) yes . . . C10 N1 H1 119.888 no . . . C10 N1 H2 120.111 no . . . H1 N1 H2 120.001 no . . . C11 N2 H3 120.238 no . . . C11 N2 H4 119.765 no . . . H3 N2 H4 119.997 no . . . C2 C1 H5 112.459 no . . . C2 C1 H6 112.046 no . . . C9 C1 H5 110.000 no . . . C9 C1 H6 110.134 no . . . H5 C1 H6 109.434 no . . . C2 C3 H7 112.715 no . . . C2 C3 H8 113.044 no . . . C4 C3 H7 109.476 no . . . C4 C3 H8 109.699 no . . . H7 C3 H8 109.375 no . . . C4 C5 H9 119.837 no . . . C6 C5 H9 120.995 no . . . C7 C8 H10 120.387 no . . . C9 C8 H10 120.543 no . . . O3 C12 H11 109.796 no . . . O3 C12 H13 108.866 no . . . O3 C12 H12 109.674 no . . . H11 C12 H13 109.444 no . . . H11 C12 H12 108.998 no . . . H13 C12 H12 110.052 no . . . O4 C13 H15 102.792 no . . . O4 C13 H14 109.493 no . . . O4 C13 H16 109.347 no . . . H15 C13 H14 112.765 no . . . H15 C13 H16 112.756 no . . . H14 C13 H16 109.446 no . . . 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_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C12 O3 C6 C5 3.8(4) no . . . . C12 O3 C6 C7 -177.0(3) no . . . . C13 O4 C7 C6 -169.6(3) no . . . . C13 O4 C7 C8 10.3(4) no . . . . C2 C1 C9 C4 -19.4(3) no . . . . C2 C1 C9 C8 165.2(3) no . . . . C9 C1 C2 C3 31.1(3) no . . . . C9 C1 C2 C10 -88.6(2) no . . . . C9 C1 C2 C11 154.37(19) no . . . . C1 C2 C3 C4 -31.4(3) no . . . . C1 C2 C10 O1 -22.5(3) no . . . . C1 C2 C10 N1 160.88(18) no . . . . C1 C2 C11 O2 -140.3(3) no . . . . C1 C2 C11 N2 42.7(3) no . . . . C3 C2 C10 O1 -137.0(2) no . . . . C3 C2 C10 N1 46.3(3) no . . . . C10 C2 C3 C4 87.0(2) no . . . . C3 C2 C11 O2 -22.5(4) no . . . . C3 C2 C11 N2 160.4(2) no . . . . C11 C2 C3 C4 -154.96(18) no . . . . C10 C2 C11 O2 99.6(3) no . . . . C10 C2 C11 N2 -77.4(3) no . . . . C11 C2 C10 O1 99.9(3) no . . . . C11 C2 C10 N1 -76.7(3) no . . . . C2 C3 C4 C5 -162.8(3) no . . . . C2 C3 C4 C9 20.6(3) no . . . . C3 C4 C5 C6 -174.9(3) no . . . . C3 C4 C9 C1 -0.8(3) no . . . . C3 C4 C9 C8 175.0(2) no . . . . C5 C4 C9 C1 -177.7(3) no . . . . C5 C4 C9 C8 -2.0(4) no . . . . C9 C4 C5 C6 1.4(4) no . . . . C4 C5 C6 O3 -180.0(3) no . . . . C4 C5 C6 C7 0.9(5) no . . . . O3 C6 C7 O4 -1.9(4) no . . . . O3 C6 C7 C8 178.2(3) no . . . . C5 C6 C7 O4 177.3(3) no . . . . C5 C6 C7 C8 -2.6(5) no . . . . O4 C7 C8 C9 -177.9(3) no . . . . C6 C7 C8 C9 2.0(4) no . . . . C7 C8 C9 C1 175.2(3) no . . . . C7 C8 C9 C4 0.2(4) no . . . . #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #============================================================================== data_101221hk _database_code_depnum_ccdc_archive 'CCDC 805783' #TrackingRef '47MeO_disorder.cif' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C13 H16 N2 O4' _chemical_formula_moiety 'C13 H16 N2 O4' _chemical_formula_weight 264.28 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1' _symmetry_space_group_name_Hall '-C 2yc' _symmetry_Int_Tables_number 15 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,+Y,1/2-Z 3 -X,-Y,-Z 4 +X,-Y,1/2+Z 5 1/2+X,1/2+Y,+Z 6 1/2-X,1/2+Y,1/2-Z 7 1/2-X,1/2-Y,-Z 8 1/2+X,1/2-Y,1/2+Z #------------------------------------------------------------------------------ _cell_length_a 18.328(5) _cell_length_b 6.5775(14) _cell_length_c 22.617(6) _cell_angle_alpha 90.0000 _cell_angle_beta 110.443(4) _cell_angle_gamma 90.0000 _cell_volume 2554.8(11) _cell_formula_units_Z 8 _cell_measurement_reflns_used 4046 _cell_measurement_theta_min 3.03 _cell_measurement_theta_max 27.48 _cell_measurement_temperature 123 #------------------------------------------------------------------------------ _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.500 _exptl_crystal_size_mid 0.300 _exptl_crystal_size_min 0.150 _exptl_crystal_density_diffrn 1.374 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1120.00 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'REQAB (Rigaku, 1998)' _exptl_absorpt_correction_T_min 0.871 _exptl_absorpt_correction_T_max 0.985 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 123 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71070 _diffrn_measurement_device_type 'Rigaku Mercury70' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 7.314 _diffrn_reflns_number 10193 _diffrn_reflns_av_R_equivalents 0.0225 _diffrn_reflns_theta_max 27.47 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_max 0.984 _diffrn_measured_fraction_theta_full 0.984 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 29 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_decay_% ? #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 2899 _reflns_number_gt 2702 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0480 _refine_ls_wR_factor_ref 0.1794 _refine_ls_number_restraints ? _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 2899 _refine_ls_number_parameters 198 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[0.0064Fo^2^ + 1.0000\s(Fo^2^)]/(4Fo^2^)' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_diff_density_max 0.448 _refine_diff_density_min -0.246 _refine_ls_extinction_method none _refine_ls_extinction_coef ? 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 for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.0000 0.0000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; N N 0.0061 0.0033 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.0106 0.0060 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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 0.07051(4) 0.21810(11) 0.48614(4) 0.0215(3) Uani 1.0 8 d . . . O2 O 0.21319(5) -0.33363(12) 0.54905(4) 0.0303(3) Uani 1.0 8 d . . . O3 O 0.33963(4) 0.37101(13) 0.67228(4) 0.0242(3) Uani 1.0 8 d . . . O4 O 0.03443(5) 0.33437(12) 0.66723(5) 0.0330(3) Uani 1.0 8 d . . . N1 N 0.16293(6) 0.05311(14) 0.46092(5) 0.0268(3) Uani 1.0 8 d . . . N2 N 0.08438(6) -0.34846(13) 0.52851(5) 0.0289(3) Uani 1.0 8 d . . . C1 C 0.09825(6) 0.03007(15) 0.60091(5) 0.0194(3) Uani 1.0 8 d . . . C2 C 0.15087(6) -0.02562(15) 0.56248(5) 0.0174(3) Uani 1.0 8 d . . . C3 C 0.23332(6) 0.04940(15) 0.60393(5) 0.0208(3) Uani 1.0 8 d . . . C4 C 0.21533(6) 0.22291(15) 0.64021(5) 0.0192(3) Uani 1.0 8 d . . . C5 C 0.26500(6) 0.37678(16) 0.67326(5) 0.0204(3) Uani 1.0 8 d . . . C6 C 0.23660(7) 0.52100(17) 0.70521(5) 0.0243(3) Uani 1.0 8 d . . . C7 C 0.15980(7) 0.50954(17) 0.70320(6) 0.0256(3) Uani 1.0 8 d . . . C8 C 0.11011(7) 0.35632(16) 0.66992(5) 0.0226(3) Uani 1.0 8 d . . . C9 C 0.13912(6) 0.21211(15) 0.63845(5) 0.0193(3) Uani 1.0 8 d . . . C10 C 0.12429(6) 0.09314(14) 0.49949(5) 0.0170(3) Uani 1.0 8 d . . . C11 C 0.15219(6) -0.25147(15) 0.54650(5) 0.0199(3) Uani 1.0 8 d . . . C12 C 0.38957(8) 0.5359(2) 0.70231(7) 0.0362(4) Uani 1.0 8 d . . . C13 C -0.00628(19) 0.5149(5) 0.67156(19) 0.0481(9) Uani 0.6500 8 d . . . C14 C -0.0164(3) 0.4736(10) 0.6403(3) 0.0436(15) Uani 0.3500 8 d . . . H1 H 0.1500 0.1201 0.4224 0.0330 Uiso 1.0 8 calc R . . H2 H 0.2030 -0.0420 0.4725 0.0349 Uiso 1.0 8 calc R . . H3 H 0.0819 -0.4849 0.5172 0.0361 Uiso 1.0 8 calc R . . H4 H 0.0394 -0.2801 0.5273 0.0360 Uiso 1.0 8 calc R . . H5 H 0.0458 0.0664 0.5743 0.0235 Uiso 1.0 8 calc R . . H6 H 0.0961 -0.0783 0.6294 0.0248 Uiso 1.0 8 calc R . . H7 H 0.2629 -0.0540 0.6331 0.0247 Uiso 1.0 8 calc R . . H8 H 0.2634 0.0986 0.5791 0.0254 Uiso 1.0 8 calc R . . H9 H 0.2692 0.6243 0.7277 0.0284 Uiso 1.0 8 calc R . . H10 H 0.1413 0.6057 0.7247 0.0315 Uiso 1.0 8 calc R . . H11 H 0.3998 0.5243 0.7508 0.0433 Uiso 1.0 8 calc R . . H12 H 0.3648 0.6612 0.6862 0.0433 Uiso 1.0 8 calc R . . H13 H 0.4370 0.5259 0.6944 0.0423 Uiso 1.0 8 calc R . . H14 H -0.0668 0.4607 0.6494 0.0622 Uiso 1.0 8 calc R . . H15 H 0.0229 0.5505 0.7136 0.0624 Uiso 0.6500 8 calc R . . H16 H -0.0016 0.6276 0.6486 0.0621 Uiso 1.0 8 calc R . . H17 H -0.0060 0.5116 0.6001 0.0544 Uiso 0.3500 8 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 0.0191(5) 0.0188(4) 0.0262(5) 0.0054(3) 0.0072(4) -0.0004(3) O2 0.0251(5) 0.0237(5) 0.0479(6) 0.0085(3) 0.0201(5) 0.0028(4) O3 0.0192(5) 0.0311(5) 0.0213(5) -0.0048(3) 0.0056(4) -0.0018(3) O4 0.0245(5) 0.0251(5) 0.0544(7) 0.0006(4) 0.0201(5) -0.0065(4) N1 0.0296(6) 0.0307(6) 0.0242(6) 0.0139(4) 0.0145(5) 0.0070(4) N2 0.0223(6) 0.0162(5) 0.0500(7) 0.0019(4) 0.0150(5) -0.0075(4) C1 0.0189(6) 0.0189(5) 0.0224(6) -0.0001(4) 0.0096(5) -0.0001(4) C2 0.0155(6) 0.0163(5) 0.0214(6) 0.0013(4) 0.0078(5) 0.0008(4) C3 0.0169(6) 0.0237(6) 0.0214(6) 0.0006(4) 0.0063(5) -0.0010(4) C4 0.0196(6) 0.0212(6) 0.0157(6) 0.0008(4) 0.0049(4) 0.0030(4) C5 0.0197(6) 0.0244(6) 0.0158(6) -0.0011(4) 0.0046(5) 0.0031(4) C6 0.0256(6) 0.0241(6) 0.0213(6) -0.0030(4) 0.0058(5) -0.0020(4) C7 0.0284(7) 0.0232(6) 0.0259(7) 0.0012(5) 0.0103(5) -0.0035(4) C8 0.0219(6) 0.0232(6) 0.0238(6) 0.0010(4) 0.0093(5) -0.0001(4) C9 0.0209(6) 0.0195(5) 0.0178(6) 0.0004(4) 0.0071(5) 0.0022(4) C10 0.0163(5) 0.0138(5) 0.0199(6) -0.0005(4) 0.0052(4) -0.0033(4) C11 0.0222(6) 0.0165(5) 0.0238(6) 0.0043(4) 0.0115(5) 0.0026(4) C12 0.0237(7) 0.0363(7) 0.0469(9) -0.0112(5) 0.0103(6) -0.0094(6) C13 0.0371(16) 0.0321(12) 0.086(3) 0.0064(10) 0.0349(19) -0.0043(16) C14 0.027(3) 0.054(4) 0.055(4) 0.015(2) 0.021(3) 0.027(3) #============================================================================== _computing_data_collection 'CrystalClear (Rigaku Corp., 2000)' _computing_cell_refinement CrystalClear _computing_data_reduction CrystalClear _computing_structure_solution SIR97 _computing_structure_refinement 'CRYSTALS (Carruthers, et al., 1999)' _computing_publication_material 'CrystalStructure 4.0 (Rigaku, 2010)' _computing_molecular_graphics 'CrystalStructure 4.0' #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 O1 C10 1.2371(13) yes . . O2 C11 1.2249(15) yes . . O3 C5 1.3763(15) yes . . O3 C12 1.4289(15) yes . . O4 C8 1.3746(17) yes . . O4 C13 1.424(4) yes . . O4 C14 1.296(6) yes . . N1 C10 1.3279(19) yes . . N2 C11 1.3281(15) yes . . C1 C2 1.5509(19) yes . . C1 C9 1.5071(14) yes . . C2 C3 1.5545(14) yes . . C2 C10 1.5467(15) yes . . C2 C11 1.5310(15) yes . . C3 C4 1.5078(16) yes . . C4 C5 1.3916(14) yes . . C4 C9 1.3852(17) yes . . C5 C6 1.3985(18) yes . . C6 C7 1.394(2) yes . . C7 C8 1.3903(16) yes . . C8 C9 1.3976(18) yes . . C13 C14 0.718(8) yes . . N1 H1 0.930 no . . N1 H2 0.930 no . . N2 H3 0.930 no . . N2 H4 0.930 no . . C1 H5 0.970 no . . C1 H6 0.970 no . . C3 H7 0.970 no . . C3 H8 0.970 no . . C6 H9 0.930 no . . C7 H10 0.930 no . . C12 H11 1.049 no . . C12 H12 0.950 no . . C12 H13 0.950 no . . C13 H14 1.105 no . . C13 H15 0.943 no . . C13 H16 0.927 no . . C14 H14 1.017 no . . C14 H16 1.049 no . . C14 H17 1.024 no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 C5 O3 C12 116.53(11) yes . . . C8 O4 C13 117.02(16) yes . . . C8 O4 C14 119.7(3) yes . . . C13 O4 C14 30.1(4) yes . . . C2 C1 C9 102.67(9) yes . . . C1 C2 C3 104.53(9) yes . . . C1 C2 C10 109.84(9) yes . . . C1 C2 C11 115.19(10) yes . . . C3 C2 C10 108.80(9) yes . . . C3 C2 C11 110.99(9) yes . . . C10 C2 C11 107.37(9) yes . . . C2 C3 C4 102.54(9) yes . . . C3 C4 C5 128.06(11) yes . . . C3 C4 C9 110.83(9) yes . . . C5 C4 C9 121.11(11) yes . . . O3 C5 C4 116.02(11) yes . . . O3 C5 C6 125.34(10) yes . . . C4 C5 C6 118.63(11) yes . . . C5 C6 C7 120.01(10) yes . . . C6 C7 C8 121.32(13) yes . . . O4 C8 C7 124.07(12) yes . . . O4 C8 C9 117.62(10) yes . . . C7 C8 C9 118.29(12) yes . . . C1 C9 C4 110.78(10) yes . . . C1 C9 C8 128.57(11) yes . . . C4 C9 C8 120.64(10) yes . . . O1 C10 N1 122.26(11) yes . . . O1 C10 C2 121.88(12) yes . . . N1 C10 C2 115.86(9) yes . . . O2 C11 N2 122.93(10) yes . . . O2 C11 C2 120.42(10) yes . . . N2 C11 C2 116.62(10) yes . . . O4 C13 C14 65.0(5) yes . . . O4 C14 C13 84.8(6) yes . . . C10 N1 H1 120.123 no . . . C10 N1 H2 119.878 no . . . H1 N1 H2 120.000 no . . . C11 N2 H3 119.940 no . . . C11 N2 H4 120.056 no . . . H3 N2 H4 120.004 no . . . C2 C1 H5 112.698 no . . . C2 C1 H6 112.019 no . . . C9 C1 H5 110.141 no . . . C9 C1 H6 109.715 no . . . H5 C1 H6 109.410 no . . . C2 C3 H7 112.470 no . . . C2 C3 H8 112.677 no . . . C4 C3 H7 109.714 no . . . C4 C3 H8 109.851 no . . . H7 C3 H8 109.380 no . . . C5 C6 H9 119.565 no . . . C7 C6 H9 120.424 no . . . C6 C7 H10 119.582 no . . . C8 C7 H10 119.100 no . . . O3 C12 H11 106.990 no . . . O3 C12 H12 109.598 no . . . O3 C12 H13 109.498 no . . . H11 C12 H12 110.634 no . . . H11 C12 H13 110.632 no . . . H12 C12 H13 109.449 no . . . O4 C13 H14 99.604 no . . . O4 C13 H15 98.634 no . . . O4 C13 H16 118.353 no . . . C14 C13 H14 63.749 no . . . C14 C13 H15 161.109 no . . . C14 C13 H16 78.101 no . . . H14 C13 H15 131.604 no . . . H14 C13 H16 106.189 no . . . H15 C13 H16 103.626 no . . . O4 C14 H14 113.668 no . . . O4 C14 H16 120.013 no . . . O4 C14 H17 105.227 no . . . C13 C14 H14 76.980 no . . . C13 C14 H16 59.863 no . . . C13 C14 H17 135.867 no . . . H14 C14 H16 104.013 no . . . H14 C14 H17 131.540 no . . . H16 C14 H17 78.748 no . . . C13 H14 C14 39.271 no . . . C13 H16 C14 42.036 no . . . 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_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C12 O3 C5 C4 175.78(9) no . . . . C12 O3 C5 C6 -5.30(15) no . . . . C8 O4 C13 C14 103.2(3) no . . . . C13 O4 C8 C7 30.4(3) no . . . . C13 O4 C8 C9 -151.3(2) no . . . . C8 O4 C14 C13 -93.4(6) no . . . . C14 O4 C8 C7 64.7(4) no . . . . C14 O4 C8 C9 -117.0(4) no . . . . C13 O4 C14 C13 0.0(3) no . . . . C14 O4 C13 C14 0.0(6) no . . . . C2 C1 C9 C4 -17.96(10) no . . . . C2 C1 C9 C8 163.28(9) no . . . . C9 C1 C2 C3 27.96(9) no . . . . C9 C1 C2 C10 -88.62(8) no . . . . C9 C1 C2 C11 150.02(7) no . . . . C1 C2 C3 C4 -27.88(9) no . . . . C1 C2 C10 O1 2.72(12) no . . . . C1 C2 C10 N1 -177.52(7) no . . . . C1 C2 C11 O2 -140.07(10) no . . . . C1 C2 C11 N2 41.68(12) no . . . . C3 C2 C10 O1 -111.14(11) no . . . . C3 C2 C10 N1 68.61(11) no . . . . C10 C2 C3 C4 89.42(10) no . . . . C3 C2 C11 O2 -21.55(15) no . . . . C3 C2 C11 N2 160.20(9) no . . . . C11 C2 C3 C4 -152.66(9) no . . . . C10 C2 C11 O2 97.24(11) no . . . . C10 C2 C11 N2 -81.01(12) no . . . . C11 C2 C10 O1 128.66(10) no . . . . C11 C2 C10 N1 -51.58(11) no . . . . C2 C3 C4 C5 -163.44(9) no . . . . C2 C3 C4 C9 17.75(11) no . . . . C3 C4 C5 O3 0.62(16) no . . . . C3 C4 C5 C6 -178.38(9) no . . . . C3 C4 C9 C1 0.10(12) no . . . . C3 C4 C9 C8 178.97(8) no . . . . C5 C4 C9 C1 -178.80(9) no . . . . C5 C4 C9 C8 0.07(15) no . . . . C9 C4 C5 O3 179.32(9) no . . . . C9 C4 C5 C6 0.32(15) no . . . . O3 C5 C6 C7 -179.30(9) no . . . . C4 C5 C6 C7 -0.41(15) no . . . . C5 C6 C7 C8 0.11(17) no . . . . C6 C7 C8 O4 178.58(10) no . . . . C6 C7 C8 C9 0.28(17) no . . . . O4 C8 C9 C1 -0.13(16) no . . . . O4 C8 C9 C4 -178.78(9) no . . . . C7 C8 C9 C1 178.28(10) no . . . . C7 C8 C9 C4 -0.37(15) no . . . . O4 C13 C14 O4 0.00(5) no . . . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 O1 C1 2.7575(15) no . . O1 C3 3.4176(13) no . . O1 C4 3.5676(14) no . . O1 C9 3.2285(16) no . . O1 C11 3.4952(14) no . . O2 N1 3.1638(14) no . . O2 C3 2.7756(14) no . . O2 C10 3.2427(14) no . . O3 C3 2.9252(13) no . . O4 C1 2.9749(17) no . . N1 N2 3.5949(17) no . . N1 C3 3.0351(17) no . . N1 C11 2.8398(17) no . . N2 C1 2.9418(15) no . . N2 C10 3.1206(15) no . . C4 C7 2.7627(19) no . . C4 C10 3.1516(16) no . . C5 C8 2.8166(19) no . . C6 C9 2.7777(15) no . . C6 C12 2.829(3) no . . C7 C13 2.874(4) no . . C7 C14 3.049(6) no . . C9 C10 3.1570(18) no . . C9 C14 3.342(7) no . . O1 N2 2.9901(13) no . 1_565 O1 N2 2.8718(15) no . 3_556 O1 C1 3.4430(13) no . 3_556 O1 C14 3.361(7) no . 3_566 O2 O2 3.1694(16) no . 7_546 O2 O3 3.5215(12) no . 1_545 O2 N1 2.7655(16) no . 7_546 O2 C4 3.5642(15) no . 1_545 O2 C5 3.2493(15) no . 1_545 O2 C6 3.5375(17) no . 1_545 O3 O2 3.5215(12) no . 1_565 O3 N1 3.0378(17) no . 7_556 O4 C12 3.4100(18) no . 6_546 N1 O2 2.7655(16) no . 7_546 N1 O3 3.0378(17) no . 7_556 N1 C12 3.524(2) no . 7_556 N2 O1 2.9901(13) no . 1_545 N2 O1 2.8718(15) no . 3_556 N2 N2 3.5239(15) no . 3_546 C1 O1 3.4430(13) no . 3_556 C4 O2 3.5642(15) no . 1_565 C4 C6 3.5512(18) no . 6_546 C5 O2 3.2493(15) no . 1_565 C5 C7 3.5848(17) no . 6_546 C6 O2 3.5375(17) no . 1_565 C6 C4 3.5512(18) no . 6_556 C7 C5 3.5848(17) no . 6_556 C8 C12 3.575(2) no . 6_546 C12 O4 3.4100(18) no . 6_556 C12 N1 3.524(2) no . 7_556 C12 C8 3.575(2) no . 6_556 C13 C13 3.474(7) no . 2_556 C14 O1 3.361(7) no . 3_566 O1 H1 2.4668 no . . O1 H2 3.0728 no . . O1 H4 3.5064 no . . O1 H5 2.4094 no . . O1 H8 3.5130 no . . O2 H2 2.5467 no . . O2 H3 2.4682 no . . O2 H4 3.0677 no . . O2 H7 2.5721 no . . O2 H8 2.9921 no . . O3 H7 3.1155 no . . O3 H8 2.7479 no . . O3 H9 2.6719 no . . O4 H5 2.8065 no . . O4 H6 3.1713 no . . O4 H10 2.6329 no . . N1 H8 2.6799 no . . N2 H2 3.5098 no . . N2 H5 3.0869 no . . N2 H6 2.8395 no . . C1 H4 2.6161 no . . C1 H7 2.8997 no . . C1 H8 3.2637 no . . C2 H1 3.3047 no . . C2 H2 2.5345 no . . C2 H3 3.2970 no . . C2 H4 2.5435 no . . C3 H2 2.8898 no . . C3 H5 3.2663 no . . C3 H6 2.8930 no . . C4 H5 3.1154 no . . C4 H6 2.8956 no . . C4 H9 3.2394 no . . C5 H7 2.9716 no . . C5 H8 2.8007 no . . C5 H10 3.2553 no . . C5 H11 2.6632 no . . C5 H12 2.5616 no . . C5 H13 3.1747 no . . C6 H11 2.8024 no . . C6 H12 2.6961 no . . C7 H15 2.6146 no . . C7 H16 2.8851 no . . C7 H17 3.1174 no . . C8 H5 2.8153 no . . C8 H6 2.9860 no . . C8 H9 3.2645 no . . C8 H14 3.1854 no . . C8 H15 2.5030 no . . C8 H16 2.6299 no . . C8 H17 2.3905 no . . C9 H7 2.9013 no . . C9 H8 3.1122 no . . C9 H10 3.2325 no . . C9 H17 3.1766 no . . C10 H4 3.0854 no . . C10 H5 2.5812 no . . C10 H6 3.3503 no . . C10 H7 3.3401 no . . C10 H8 2.5562 no . . C11 H2 2.5798 no . . C11 H5 3.0702 no . . C11 H6 2.6851 no . . C11 H7 2.6198 no . . C11 H8 2.9914 no . . C12 H9 2.5329 no . . C13 H10 2.6169 no . . C14 H5 3.4487 no . . C14 H10 2.9825 no . . H1 H8 3.4276 no . . H2 H7 3.4078 no . . H2 H8 2.4543 no . . H4 H5 2.5001 no . . H4 H6 2.5490 no . . H5 H17 3.1938 no . . H6 H7 3.0326 no . . H9 H10 2.3245 no . . H9 H11 2.3574 no . . H9 H12 2.2718 no . . H9 H13 3.4733 no . . H10 H15 2.1276 no . . H10 H16 2.5868 no . . H10 H17 3.2082 no . . H15 H17 2.4469 no . . O1 H3 2.0616 no . 1_565 O1 H3 3.2768 no . 3_556 O1 H4 3.5290 no . 1_565 O1 H4 1.9731 no . 3_556 O1 H5 2.8063 no . 3_556 O1 H6 3.3800 no . 3_556 O1 H16 3.0366 no . 3_566 O1 H17 2.5989 no . 3_566 O2 H1 3.0202 no . 7_546 O2 H2 1.9466 no . 7_546 O2 H8 3.5335 no . 7_546 O2 H12 3.3647 no . 1_545 O3 H1 2.2155 no . 7_556 O3 H2 3.2880 no . 7_556 O3 H10 2.8342 no . 6_546 O3 H14 3.3340 no . 5_545 O3 H15 3.5933 no . 6_546 O3 H16 3.5231 no . 5_545 O4 H11 2.7366 no . 6_546 O4 H12 3.4743 no . 5_445 O4 H12 3.3801 no . 6_546 O4 H13 2.9063 no . 5_445 O4 H15 3.5165 no . 2_556 N1 H8 2.9570 no . 7_556 N1 H12 3.4825 no . 7_556 N1 H13 3.3858 no . 7_556 N2 H3 3.0583 no . 3_546 N2 H4 3.2730 no . 3_546 N2 H5 3.2652 no . 3_556 N2 H16 3.5872 no . 1_545 N2 H17 2.8430 no . 1_545 N2 H17 2.9593 no . 3_556 C1 H4 3.5164 no . 3_556 C1 H11 3.3415 no . 6_546 C1 H16 3.5908 no . 1_545 C3 H1 3.2469 no . 7_556 C3 H12 3.5575 no . 1_545 C3 H14 3.4913 no . 5_545 C4 H1 3.4064 no . 7_556 C4 H3 3.5586 no . 1_565 C4 H9 2.9732 no . 6_546 C4 H10 3.3511 no . 6_546 C5 H1 3.0759 no . 7_556 C5 H9 3.0256 no . 6_546 C5 H10 2.9478 no . 6_546 C6 H7 3.3555 no . 1_565 C6 H9 3.0393 no . 6_546 C6 H10 3.5363 no . 6_546 C7 H6 3.1840 no . 1_565 C7 H7 3.4971 no . 6_556 C7 H9 3.0227 no . 6_546 C7 H12 3.5362 no . 6_546 C8 H3 3.4698 no . 1_565 C8 H9 3.0012 no . 6_546 C8 H11 2.8712 no . 6_546 C8 H12 3.3778 no . 6_546 C9 H3 3.2530 no . 1_565 C9 H9 2.9617 no . 6_546 C9 H11 3.0912 no . 6_546 C10 H3 2.9471 no . 1_565 C10 H4 3.1010 no . 3_556 C10 H5 3.1569 no . 3_556 C11 H2 3.1418 no . 7_546 C12 H1 2.8470 no . 7_556 C12 H7 3.5467 no . 1_565 C12 H10 3.4222 no . 6_546 C12 H13 3.2217 no . 2_656 C12 H14 3.2478 no . 5_555 C13 H6 3.5841 no . 1_565 C13 H12 3.4122 no . 5_445 C13 H13 3.4735 no . 5_445 C13 H15 2.7286 no . 2_556 C14 H1 3.5678 no . 3_566 C14 H3 3.3400 no . 3_556 C14 H4 3.4705 no . 1_565 C14 H12 3.4071 no . 5_445 C14 H13 3.4091 no . 5_445 C14 H15 3.3846 no . 2_556 H1 O2 3.0202 no . 7_546 H1 O3 2.2155 no . 7_556 H1 C3 3.2469 no . 7_556 H1 C4 3.4064 no . 7_556 H1 C5 3.0759 no . 7_556 H1 C12 2.8470 no . 7_556 H1 C14 3.5678 no . 3_566 H1 H8 2.4457 no . 7_556 H1 H12 3.0097 no . 7_556 H1 H13 2.7379 no . 7_556 H1 H14 3.2918 no . 3_566 H1 H16 3.1119 no . 3_566 H1 H17 3.4876 no . 3_566 H2 O2 1.9466 no . 7_546 H2 O3 3.2880 no . 7_556 H2 C11 3.1418 no . 7_546 H2 H2 3.2412 no . 7_546 H2 H8 3.2783 no . 7_556 H2 H12 3.4527 no . 7_556 H3 O1 2.0616 no . 1_545 H3 O1 3.2768 no . 3_556 H3 N2 3.0583 no . 3_546 H3 C4 3.5586 no . 1_545 H3 C8 3.4698 no . 1_545 H3 C9 3.2530 no . 1_545 H3 C10 2.9471 no . 1_545 H3 C14 3.3400 no . 3_556 H3 H3 2.8316 no . 3_546 H3 H4 2.6043 no . 3_546 H3 H5 3.3778 no . 1_545 H3 H17 2.8660 no . 1_545 H3 H17 2.5350 no . 3_556 H4 O1 3.5290 no . 1_545 H4 O1 1.9731 no . 3_556 H4 N2 3.2730 no . 3_546 H4 C1 3.5164 no . 3_556 H4 C10 3.1010 no . 3_556 H4 C14 3.4705 no . 1_545 H4 H3 2.6043 no . 3_546 H4 H4 3.2767 no . 3_546 H4 H5 2.6796 no . 3_556 H4 H16 3.1471 no . 1_545 H4 H17 2.4987 no . 1_545 H4 H17 3.1235 no . 3_556 H5 O1 2.8063 no . 3_556 H5 N2 3.2652 no . 3_556 H5 C10 3.1569 no . 3_556 H5 H3 3.3778 no . 1_565 H5 H4 2.6796 no . 3_556 H5 H5 3.3051 no . 3_556 H5 H16 3.5951 no . 1_545 H6 O1 3.3800 no . 3_556 H6 C7 3.1840 no . 1_545 H6 C13 3.5841 no . 1_545 H6 H9 3.5706 no . 6_546 H6 H10 2.8989 no . 1_545 H6 H11 2.7686 no . 6_546 H6 H16 2.7712 no . 1_545 H6 H17 3.2172 no . 1_545 H7 C6 3.3555 no . 1_545 H7 C7 3.4971 no . 6_546 H7 C12 3.5467 no . 1_545 H7 H9 2.9824 no . 1_545 H7 H9 3.5970 no . 6_546 H7 H10 3.2547 no . 6_546 H7 H12 2.6219 no . 1_545 H7 H14 3.0142 no . 5_545 H8 O2 3.5335 no . 7_546 H8 N1 2.9570 no . 7_556 H8 H1 2.4457 no . 7_556 H8 H2 3.2783 no . 7_556 H8 H14 3.0956 no . 5_545 H9 C4 2.9732 no . 6_556 H9 C5 3.0256 no . 6_556 H9 C6 3.0393 no . 6_556 H9 C7 3.0227 no . 6_556 H9 C8 3.0012 no . 6_556 H9 C9 2.9617 no . 6_556 H9 H6 3.5706 no . 6_556 H9 H7 2.9824 no . 1_565 H9 H7 3.5970 no . 6_556 H9 H9 3.5820 no . 6_546 H9 H9 3.5820 no . 6_556 H9 H10 3.5555 no . 6_556 H10 O3 2.8342 no . 6_556 H10 C4 3.3511 no . 6_556 H10 C5 2.9478 no . 6_556 H10 C6 3.5363 no . 6_556 H10 C12 3.4222 no . 6_556 H10 H6 2.8989 no . 1_565 H10 H7 3.2547 no . 6_556 H10 H9 3.5555 no . 6_546 H10 H11 2.9578 no . 6_556 H10 H12 3.5760 no . 6_546 H11 O4 2.7366 no . 6_556 H11 C1 3.3415 no . 6_556 H11 C8 2.8712 no . 6_556 H11 C9 3.0912 no . 6_556 H11 H6 2.7686 no . 6_556 H11 H10 2.9578 no . 6_546 H11 H13 2.8098 no . 2_656 H11 H15 3.4020 no . 6_546 H11 H16 3.5357 no . 6_546 H12 O2 3.3647 no . 1_565 H12 O4 3.4743 no . 5_555 H12 O4 3.3801 no . 6_556 H12 N1 3.4825 no . 7_556 H12 C3 3.5575 no . 1_565 H12 C7 3.5362 no . 6_556 H12 C8 3.3778 no . 6_556 H12 C13 3.4122 no . 5_555 H12 C14 3.4071 no . 5_555 H12 H1 3.0097 no . 7_556 H12 H2 3.4527 no . 7_556 H12 H7 2.6219 no . 1_565 H12 H10 3.5760 no . 6_556 H12 H14 2.6211 no . 5_555 H12 H15 3.5593 no . 6_556 H13 O4 2.9063 no . 5_555 H13 N1 3.3858 no . 7_556 H13 C12 3.2217 no . 2_656 H13 C13 3.4735 no . 5_555 H13 C14 3.4091 no . 5_555 H13 H1 2.7379 no . 7_556 H13 H11 2.8098 no . 2_656 H13 H13 2.7580 no . 2_656 H13 H14 3.0283 no . 5_555 H13 H15 3.4592 no . 5_545 H13 H16 3.1645 no . 5_545 H14 O3 3.3340 no . 5_455 H14 C3 3.4913 no . 5_455 H14 C12 3.2478 no . 5_445 H14 H1 3.2918 no . 3_566 H14 H7 3.0142 no . 5_455 H14 H8 3.0956 no . 5_455 H14 H12 2.6211 no . 5_445 H14 H13 3.0283 no . 5_445 H14 H15 2.9764 no . 2_556 H15 O3 3.5933 no . 6_556 H15 O4 3.5165 no . 2_556 H15 C13 2.7286 no . 2_556 H15 C14 3.3846 no . 2_556 H15 H11 3.4020 no . 6_556 H15 H12 3.5593 no . 6_546 H15 H13 3.4592 no . 5_455 H15 H14 2.9764 no . 2_556 H15 H15 2.0927 no . 2_556 H15 H16 3.3131 no . 2_556 H16 O1 3.0366 no . 3_566 H16 O3 3.5231 no . 5_455 H16 N2 3.5872 no . 1_565 H16 C1 3.5908 no . 1_565 H16 H1 3.1119 no . 3_566 H16 H4 3.1471 no . 1_565 H16 H5 3.5951 no . 1_565 H16 H6 2.7712 no . 1_565 H16 H11 3.5357 no . 6_556 H16 H13 3.1645 no . 5_455 H16 H15 3.3131 no . 2_556 H17 O1 2.5989 no . 3_566 H17 N2 2.8430 no . 1_565 H17 N2 2.9593 no . 3_556 H17 H1 3.4876 no . 3_566 H17 H3 2.8660 no . 1_565 H17 H3 2.5350 no . 3_556 H17 H4 2.4987 no . 1_565 H17 H4 3.1235 no . 3_556 H17 H6 3.2172 no . 1_565 #============================================================================== loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_D _geom_hbond_site_symmetry_H _geom_hbond_site_symmetry_A _geom_hbond_distance_DA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_angle_DHA _geom_hbond_publ_flag N1 H1 O3 . . 7_556 3.0378(17) 0.930 2.216 147.0 no N1 H2 O2 . . 7_546 2.7655(16) 0.930 1.947 145.8 no N2 H3 O1 . . 1_545 2.9901(13) 0.930 2.062 176.0 no N2 H4 O1 . . 3_556 2.8718(15) 0.930 1.973 161.9 no data__101217hk _database_code_depnum_ccdc_archive 'CCDC 805785' #TrackingRef 'Indandicarboxamide_HH_.cif' _audit_creation_date 2010-12-24 _audit_creation_method 'by CrystalStructure 4.0' _audit_update_record ? #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C11 H12 N2 O2' _chemical_formula_moiety 'C11 H12 N2 O2' _chemical_formula_weight 204.23 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 1/2-X,1/2+Y,1/2-Z 3 -X,-Y,-Z 4 1/2+X,1/2-Y,1/2+Z #------------------------------------------------------------------------------ _cell_length_a 10.153(6) _cell_length_b 8.109(4) _cell_length_c 12.906(8) _cell_angle_alpha 90.0000 _cell_angle_beta 110.708(6) _cell_angle_gamma 90.0000 _cell_volume 993.9(10) _cell_formula_units_Z 4 _cell_measurement_reflns_used 3325 _cell_measurement_theta_min 3.03 _cell_measurement_theta_max 27.48 _cell_measurement_temperature 123 #------------------------------------------------------------------------------ _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.400 _exptl_crystal_size_mid 0.300 _exptl_crystal_size_min 0.200 _exptl_crystal_density_diffrn 1.365 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 432.00 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'CrystalClear (Rigaku, ????)' _exptl_absorpt_correction_T_min 0.772 _exptl_absorpt_correction_T_max 0.981 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 123 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71070 _diffrn_measurement_device_type 'Rigaku AFC7R' _diffrn_measurement_method \w-2\q _diffrn_reflns_number 7759 _diffrn_reflns_av_R_equivalents 0.0241 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_max 0.975 _diffrn_measured_fraction_theta_full 0.975 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_decay_% 0.000 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 2226 _reflns_number_gt 1885 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0419 _refine_ls_wR_factor_ref 0.1316 _refine_ls_number_restraints ? _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 2226 _refine_ls_number_parameters 148 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[0.0021Fo^2^ + 1.0000\s(Fo^2^)]/(4Fo^2^)' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_diff_density_max 0.421 _refine_diff_density_min -0.239 _refine_ls_extinction_method none _refine_ls_extinction_coef ? 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 for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.0000 0.0000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; N N 0.0061 0.0033 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.0106 0.0060 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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 O(1) O 0.15873(9) -0.04696(10) 1.13541(7) 0.0219(3) Uani 1.0 4 d . . . O(2) O 0.20223(8) 0.45868(10) 1.05202(7) 0.0189(3) Uani 1.0 4 d . . . N(1) N 0.30957(11) 0.13296(13) 1.24874(8) 0.0217(3) Uani 1.0 4 d . . . N(2) N 0.01821(10) 0.28350(12) 1.00244(8) 0.0187(3) Uani 1.0 4 d . . . C(1) C 0.40569(12) 0.21887(14) 1.06729(10) 0.0183(3) Uani 1.0 4 d . . . C(2) C 0.25285(11) 0.16481(14) 1.04978(9) 0.0146(3) Uani 1.0 4 d . . . C(3) C 0.21080(12) 0.05356(14) 0.94532(9) 0.0176(3) Uani 1.0 4 d . . . C(4) C 0.29935(12) 0.11962(14) 0.88244(10) 0.0197(3) Uani 1.0 4 d . . . C(5) C 0.28424(14) 0.09164(17) 0.77231(11) 0.0257(4) Uani 1.0 4 d . . . C(6) C 0.38213(16) 0.16090(19) 0.73260(12) 0.0335(4) Uani 1.0 4 d . . . C(7) C 0.49330(16) 0.25480(19) 0.80186(13) 0.0354(5) Uani 1.0 4 d . . . C(8) C 0.50862(14) 0.28192(17) 0.91191(12) 0.0282(4) Uani 1.0 4 d . . . C(9) C 0.41046(12) 0.21311(14) 0.95182(10) 0.0197(3) Uani 1.0 4 d . . . C(10) C 0.23750(12) 0.07326(13) 1.14870(9) 0.0148(3) Uani 1.0 4 d . . . C(11) C 0.15504(11) 0.31625(14) 1.03303(8) 0.0142(3) Uani 1.0 4 d . . . H(1) H 0.3014 0.0826 1.3126 0.0264 Uiso 1.0 4 calc R . . H(2) H 0.3693 0.2259 1.2563 0.0266 Uiso 1.0 4 calc R . . H(3) H -0.0472 0.3705 0.9948 0.0233 Uiso 1.0 4 calc R . . H(4) H -0.0141 0.1729 0.9884 0.0230 Uiso 1.0 4 calc R . . H(5) H 0.4235 0.3272 1.0969 0.0223 Uiso 1.0 4 calc R . . H(6) H 0.4721 0.1447 1.1151 0.0215 Uiso 1.0 4 calc R . . H(7) H 0.2325 -0.0587 0.9650 0.0217 Uiso 1.0 4 calc R . . H(8) H 0.1133 0.0638 0.9031 0.0218 Uiso 1.0 4 calc R . . H(9) H 0.2088 0.0263 0.7258 0.0322 Uiso 1.0 4 calc R . . H(10) H 0.3733 0.1439 0.6576 0.0437 Uiso 1.0 4 calc R . . H(11) H 0.5592 0.3017 0.7733 0.0469 Uiso 1.0 4 calc R . . H(12) H 0.5849 0.3455 0.9590 0.0355 Uiso 1.0 4 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O(1) 0.0247(5) 0.0182(5) 0.0217(5) -0.0070(4) 0.0069(4) 0.0011(4) O(2) 0.0196(5) 0.0129(5) 0.0246(5) -0.0018(3) 0.0082(4) -0.0023(3) N(1) 0.0265(6) 0.0196(6) 0.0174(5) -0.0055(5) 0.0056(4) -0.0002(4) N(2) 0.0158(5) 0.0124(5) 0.0275(6) 0.0006(4) 0.0072(4) -0.0006(4) C(1) 0.0153(6) 0.0157(6) 0.0238(6) -0.0009(5) 0.0070(5) 0.0010(5) C(2) 0.0148(6) 0.0123(6) 0.0164(6) -0.0001(4) 0.0054(4) -0.0003(4) C(3) 0.0194(6) 0.0155(6) 0.0197(6) -0.0004(5) 0.0090(5) -0.0030(5) C(4) 0.0206(6) 0.0174(6) 0.0237(7) 0.0040(5) 0.0111(5) 0.0024(5) C(5) 0.0292(7) 0.0265(7) 0.0248(7) 0.0056(6) 0.0138(6) 0.0018(5) C(6) 0.0394(9) 0.0392(9) 0.0307(8) 0.0085(7) 0.0232(7) 0.0083(6) C(7) 0.0330(8) 0.0413(9) 0.0428(9) 0.0050(7) 0.0269(7) 0.0127(7) C(8) 0.0209(7) 0.0286(7) 0.0380(8) 0.0012(5) 0.0142(6) 0.0087(6) C(9) 0.0170(6) 0.0183(6) 0.0261(7) 0.0037(5) 0.0104(5) 0.0046(5) C(10) 0.0151(6) 0.0111(6) 0.0186(6) 0.0024(4) 0.0062(5) 0.0011(4) C(11) 0.0162(6) 0.0142(6) 0.0127(5) 0.0001(4) 0.0057(4) 0.0002(4) #============================================================================== _computing_data_collection 'CrystalClear (Rigaku Corp., 2000)' _computing_cell_refinement CrystalClear _computing_data_reduction CrystalClear _computing_structure_solution SIR97 _computing_structure_refinement 'CRYSTALS (Carruthers, et al., 1999)' _computing_publication_material 'CrystalStructure 4.0 (Rigaku, 2010)' _computing_molecular_graphics 'CrystalStructure 4.0' #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 O(1) C(10) 1.2338(15) yes . . O(2) C(11) 1.2411(15) yes . . N(1) C(10) 1.3299(15) yes . . N(2) C(11) 1.3298(17) yes . . C(1) C(2) 1.5502(19) yes . . C(1) C(9) 1.509(3) yes . . C(2) C(3) 1.5513(17) yes . . C(2) C(10) 1.5317(19) yes . . C(2) C(11) 1.5456(17) yes . . C(3) C(4) 1.507(2) yes . . C(4) C(5) 1.393(3) yes . . C(4) C(9) 1.3909(16) yes . . C(5) C(6) 1.388(3) yes . . C(6) C(7) 1.393(2) yes . . C(7) C(8) 1.391(3) yes . . C(8) C(9) 1.390(3) yes . . N(1) H(1) 0.950 no . . N(1) H(2) 0.950 no . . N(2) H(3) 0.950 no . . N(2) H(4) 0.950 no . . C(1) H(5) 0.950 no . . C(1) H(6) 0.950 no . . C(3) H(7) 0.950 no . . C(3) H(8) 0.950 no . . C(5) H(9) 0.950 no . . C(6) H(10) 0.950 no . . C(7) H(11) 0.950 no . . C(8) H(12) 0.950 no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 C(2) C(1) C(9) 103.14(9) yes . . . C(1) C(2) C(3) 104.17(11) yes . . . C(1) C(2) C(10) 114.03(9) yes . . . C(1) C(2) C(11) 110.87(10) yes . . . C(3) C(2) C(10) 111.39(10) yes . . . C(3) C(2) C(11) 112.00(8) yes . . . C(10) C(2) C(11) 104.59(11) yes . . . C(2) C(3) C(4) 103.19(10) yes . . . C(3) C(4) C(5) 128.33(11) yes . . . C(3) C(4) C(9) 110.46(12) yes . . . C(5) C(4) C(9) 121.14(14) yes . . . C(4) C(5) C(6) 118.42(12) yes . . . C(5) C(6) C(7) 120.53(16) yes . . . C(6) C(7) C(8) 120.97(17) yes . . . C(7) C(8) C(9) 118.62(13) yes . . . C(1) C(9) C(4) 110.53(12) yes . . . C(1) C(9) C(8) 129.13(11) yes . . . C(4) C(9) C(8) 120.31(13) yes . . . O(1) C(10) N(1) 121.98(12) yes . . . O(1) C(10) C(2) 121.27(10) yes . . . N(1) C(10) C(2) 116.72(11) yes . . . O(2) C(11) N(2) 122.29(11) yes . . . O(2) C(11) C(2) 121.84(10) yes . . . N(2) C(11) C(2) 115.78(10) yes . . . C(10) N(1) H(1) 119.957 no . . . C(10) N(1) H(2) 120.039 no . . . H(1) N(1) H(2) 120.004 no . . . C(11) N(2) H(3) 120.060 no . . . C(11) N(2) H(4) 119.936 no . . . H(3) N(2) H(4) 120.004 no . . . C(2) C(1) H(5) 111.023 no . . . C(2) C(1) H(6) 111.067 no . . . C(9) C(1) H(5) 110.999 no . . . C(9) C(1) H(6) 111.042 no . . . H(5) C(1) H(6) 109.461 no . . . C(2) C(3) H(7) 111.004 no . . . C(2) C(3) H(8) 111.004 no . . . C(4) C(3) H(7) 111.017 no . . . C(4) C(3) H(8) 111.061 no . . . H(7) C(3) H(8) 109.461 no . . . C(4) C(5) H(9) 120.612 no . . . C(6) C(5) H(9) 120.965 no . . . C(5) C(6) H(10) 119.701 no . . . C(7) C(6) H(10) 119.773 no . . . C(6) C(7) H(11) 119.485 no . . . C(8) C(7) H(11) 119.538 no . . . C(7) C(8) H(12) 120.686 no . . . C(9) C(8) H(12) 120.691 no . . . 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_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C(2) C(1) C(9) C(4) -17.47(11) no . . . . C(2) C(1) C(9) C(8) 164.45(10) no . . . . C(9) C(1) C(2) C(3) 27.57(10) no . . . . C(9) C(1) C(2) C(10) 149.20(9) no . . . . C(9) C(1) C(2) C(11) -93.08(10) no . . . . C(1) C(2) C(3) C(4) -27.80(10) no . . . . C(1) C(2) C(10) O(1) -140.06(11) no . . . . C(1) C(2) C(10) N(1) 42.00(14) no . . . . C(1) C(2) C(11) O(2) -11.98(15) no . . . . C(1) C(2) C(11) N(2) 171.24(9) no . . . . C(3) C(2) C(10) O(1) -22.51(15) no . . . . C(3) C(2) C(10) N(1) 159.55(9) no . . . . C(10) C(2) C(3) C(4) -151.16(8) no . . . . C(3) C(2) C(11) O(2) -127.86(11) no . . . . C(3) C(2) C(11) N(2) 55.35(14) no . . . . C(11) C(2) C(3) C(4) 92.09(11) no . . . . C(10) C(2) C(11) O(2) 111.36(11) no . . . . C(10) C(2) C(11) N(2) -65.43(11) no . . . . C(11) C(2) C(10) O(1) 98.67(12) no . . . . C(11) C(2) C(10) N(1) -79.27(12) no . . . . C(2) C(3) C(4) C(5) -164.80(10) no . . . . C(2) C(3) C(4) C(9) 18.02(11) no . . . . C(3) C(4) C(5) C(6) -177.61(10) no . . . . C(3) C(4) C(9) C(1) -0.35(13) no . . . . C(3) C(4) C(9) C(8) 177.92(9) no . . . . C(5) C(4) C(9) C(1) -177.77(10) no . . . . C(5) C(4) C(9) C(8) 0.50(17) no . . . . C(9) C(4) C(5) C(6) -0.69(18) no . . . . C(4) C(5) C(6) C(7) 0.6(2) no . . . . C(5) C(6) C(7) C(8) -0.3(3) no . . . . C(6) C(7) C(8) C(9) 0.0(2) no . . . . C(7) C(8) C(9) C(1) 177.74(11) no . . . . C(7) C(8) C(9) C(4) -0.17(18) no . . . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 O(1) N(2) 3.2295(18) no . . O(1) C(3) 2.807(2) no . . O(1) C(11) 3.223(2) no . . O(2) N(1) 3.5571(19) no . . O(2) C(1) 2.7927(19) no . . O(2) C(3) 3.575(3) no . . O(2) C(9) 3.470(2) no . . O(2) C(10) 3.337(2) no . . N(1) C(1) 2.922(3) no . . N(1) C(11) 3.0549(19) no . . N(2) C(3) 2.977(2) no . . N(2) C(10) 2.9076(17) no . . C(4) C(7) 2.758(3) no . . C(4) C(11) 3.237(3) no . . C(5) C(8) 2.813(2) no . . C(6) C(9) 2.773(3) no . . C(9) C(11) 3.232(3) no . . O(1) N(1) 2.9555(18) no . 2_547 O(1) N(2) 2.7948(15) no . 3_557 O(1) C(3) 3.521(3) no . 3_557 O(2) N(1) 2.974(2) no . 2_557 O(2) N(2) 2.9599(17) no . 3_567 O(2) C(8) 3.506(3) no . 3_667 N(1) O(1) 2.9555(18) no . 2_557 N(1) O(2) 2.974(2) no . 2_547 N(1) N(2) 3.281(2) no . 4_555 N(2) O(1) 2.7948(15) no . 3_557 N(2) O(2) 2.9599(17) no . 3_567 N(2) N(1) 3.281(2) no . 4_454 N(2) N(2) 3.529(3) no . 3_567 C(3) O(1) 3.521(3) no . 3_557 C(8) O(2) 3.506(3) no . 3_667 O(1) H(1) 2.4679 no . . O(1) H(2) 3.0886 no . . O(1) H(4) 2.7392 no . . O(1) H(7) 2.5636 no . . O(1) H(8) 3.0051 no . . O(2) H(2) 3.1985 no . . O(2) H(3) 2.4792 no . . O(2) H(4) 3.0971 no . . O(2) H(5) 2.3662 no . . N(1) H(5) 3.0434 no . . N(1) H(6) 2.7781 no . . N(2) H(8) 2.5738 no . . C(1) H(2) 2.5942 no . . C(1) H(7) 2.8740 no . . C(1) H(8) 3.2305 no . . C(1) H(12) 2.8495 no . . C(2) H(1) 3.3188 no . . C(2) H(2) 2.5534 no . . C(2) H(3) 3.3223 no . . C(2) H(4) 2.5414 no . . C(3) H(4) 2.7123 no . . C(3) H(5) 3.2296 no . . C(3) H(6) 2.8766 no . . C(3) H(9) 2.8352 no . . C(4) H(5) 3.1016 no . . C(4) H(6) 2.9002 no . . C(4) H(10) 3.2501 no . . C(4) H(12) 3.2730 no . . C(5) H(7) 2.9785 no . . C(5) H(8) 2.8258 no . . C(5) H(11) 3.2664 no . . C(6) H(12) 3.2807 no . . C(7) H(9) 3.2762 no . . C(8) H(5) 2.8361 no . . C(8) H(6) 2.9903 no . . C(8) H(10) 3.2748 no . . C(9) H(7) 2.8930 no . . C(9) H(8) 3.1021 no . . C(9) H(9) 3.2823 no . . C(9) H(11) 3.2504 no . . C(10) H(4) 2.7786 no . . C(10) H(5) 3.0245 no . . C(10) H(6) 2.6317 no . . C(10) H(7) 2.5854 no . . C(10) H(8) 2.9693 no . . C(11) H(2) 3.0233 no . . C(11) H(5) 2.5551 no . . C(11) H(6) 3.3175 no . . C(11) H(7) 3.3351 no . . C(11) H(8) 2.5845 no . . H(1) H(6) 3.5889 no . . H(2) H(5) 2.4520 no . . H(2) H(6) 2.4877 no . . H(3) H(8) 3.4068 no . . H(4) H(7) 3.2282 no . . H(4) H(8) 2.1618 no . . H(5) H(12) 2.8181 no . . H(6) H(7) 3.0099 no . . H(6) H(12) 3.1076 no . . H(7) H(9) 3.0889 no . . H(8) H(9) 2.8002 no . . H(9) H(10) 2.3474 no . . H(10) H(11) 2.3319 no . . H(11) H(12) 2.3438 no . . O(1) H(1) 3.0733 no . 2_547 O(1) H(2) 2.3891 no . 2_547 O(1) H(3) 3.1058 no . 3_557 O(1) H(4) 2.0232 no . 3_557 O(1) H(8) 2.6309 no . 3_557 O(1) H(11) 3.3867 no . 3_657 O(1) H(11) 3.0685 no . 4_455 O(2) H(1) 2.0266 no . 2_557 O(2) H(2) 3.5510 no . 2_557 O(2) H(3) 2.0219 no . 3_567 O(2) H(4) 3.4843 no . 3_567 O(2) H(10) 2.9490 no . 2_556 O(2) H(11) 3.2957 no . 3_667 O(2) H(12) 2.7252 no . 3_667 N(1) H(3) 2.9894 no . 4_555 N(1) H(4) 3.3666 no . 4_555 N(1) H(11) 2.7226 no . 4_455 N(2) H(1) 3.4410 no . 2_557 N(2) H(1) 2.8657 no . 4_454 N(2) H(2) 2.9976 no . 4_454 N(2) H(3) 2.8196 no . 3_567 N(2) H(7) 3.2763 no . 3_557 N(2) H(8) 3.5142 no . 3_557 N(2) H(10) 2.9336 no . 4_455 N(2) H(11) 3.4415 no . 4_455 C(1) H(12) 3.5531 no . 3_667 C(2) H(4) 3.5740 no . 3_557 C(3) H(4) 3.0498 no . 3_557 C(3) H(10) 3.5669 no . 2_546 C(4) H(6) 3.1511 no . 3_657 C(4) H(9) 3.5708 no . 2_556 C(5) H(6) 3.0600 no . 3_657 C(5) H(9) 3.5252 no . 2_556 C(6) H(3) 3.3993 no . 4_554 C(6) H(6) 3.1841 no . 3_657 C(6) H(7) 3.3058 no . 2_556 C(6) H(9) 3.2049 no . 2_556 C(7) H(1) 3.3518 no . 4_554 C(7) H(6) 3.3914 no . 3_657 C(7) H(8) 3.5245 no . 2_556 C(7) H(9) 2.9441 no . 2_556 C(8) H(5) 3.2537 no . 3_667 C(8) H(6) 3.4897 no . 3_657 C(8) H(7) 3.1232 no . 3_657 C(8) H(9) 3.0305 no . 2_556 C(9) H(6) 3.3641 no . 3_657 C(9) H(9) 3.3477 no . 2_556 C(10) H(2) 3.3989 no . 2_547 C(10) H(4) 3.0695 no . 3_557 C(10) H(8) 3.5611 no . 3_557 C(10) H(11) 2.9917 no . 4_455 C(11) H(1) 2.8642 no . 2_557 C(11) H(3) 2.7386 no . 3_567 C(11) H(10) 3.5632 no . 2_556 H(1) O(1) 3.0733 no . 2_557 H(1) O(2) 2.0266 no . 2_547 H(1) N(2) 3.4410 no . 2_547 H(1) N(2) 2.8657 no . 4_555 H(1) C(7) 3.3518 no . 4_455 H(1) C(11) 2.8642 no . 2_547 H(1) H(2) 3.3272 no . 2_547 H(1) H(3) 3.3126 no . 2_547 H(1) H(3) 2.3410 no . 4_555 H(1) H(4) 3.0952 no . 4_555 H(1) H(5) 3.5704 no . 2_547 H(1) H(11) 2.5102 no . 4_455 H(1) H(12) 3.4163 no . 4_455 H(2) O(1) 2.3891 no . 2_557 H(2) O(2) 3.5510 no . 2_547 H(2) N(2) 2.9976 no . 4_555 H(2) C(10) 3.3989 no . 2_557 H(2) H(1) 3.3272 no . 2_557 H(2) H(3) 2.9932 no . 4_555 H(2) H(4) 2.9221 no . 4_555 H(2) H(8) 3.0523 no . 4_555 H(2) H(11) 3.2398 no . 4_455 H(3) O(1) 3.1058 no . 3_557 H(3) O(2) 2.0219 no . 3_567 H(3) N(1) 2.9894 no . 4_454 H(3) N(2) 2.8196 no . 3_567 H(3) C(6) 3.3993 no . 4_455 H(3) C(11) 2.7386 no . 3_567 H(3) H(1) 3.3126 no . 2_557 H(3) H(1) 2.3410 no . 4_454 H(3) H(2) 2.9932 no . 4_454 H(3) H(3) 2.2920 no . 3_567 H(3) H(7) 3.3002 no . 3_557 H(3) H(10) 2.5059 no . 4_455 H(4) O(1) 2.0232 no . 3_557 H(4) O(2) 3.4843 no . 3_567 H(4) N(1) 3.3666 no . 4_454 H(4) C(2) 3.5740 no . 3_557 H(4) C(3) 3.0498 no . 3_557 H(4) C(10) 3.0695 no . 3_557 H(4) H(1) 3.0952 no . 4_454 H(4) H(2) 2.9221 no . 4_454 H(4) H(4) 2.8239 no . 3_557 H(4) H(7) 2.6607 no . 3_557 H(4) H(8) 2.7671 no . 3_557 H(4) H(10) 3.1700 no . 4_455 H(4) H(11) 3.4906 no . 4_455 H(5) C(8) 3.2537 no . 3_667 H(5) H(1) 3.5704 no . 2_557 H(5) H(9) 3.0263 no . 4_555 H(5) H(11) 3.4175 no . 3_667 H(5) H(12) 2.7433 no . 3_667 H(6) C(4) 3.1511 no . 3_657 H(6) C(5) 3.0600 no . 3_657 H(6) C(6) 3.1841 no . 3_657 H(6) C(7) 3.3914 no . 3_657 H(6) C(8) 3.4897 no . 3_657 H(6) C(9) 3.3641 no . 3_657 H(6) H(7) 3.5700 no . 3_657 H(6) H(9) 3.4542 no . 3_657 H(6) H(9) 3.5361 no . 4_555 H(7) N(2) 3.2763 no . 3_557 H(7) C(6) 3.3058 no . 2_546 H(7) C(8) 3.1232 no . 3_657 H(7) H(3) 3.3002 no . 3_557 H(7) H(4) 2.6607 no . 3_557 H(7) H(6) 3.5700 no . 3_657 H(7) H(10) 2.8753 no . 2_546 H(7) H(12) 2.9187 no . 3_657 H(8) O(1) 2.6309 no . 3_557 H(8) N(2) 3.5142 no . 3_557 H(8) C(7) 3.5245 no . 2_546 H(8) C(10) 3.5611 no . 3_557 H(8) H(2) 3.0523 no . 4_454 H(8) H(4) 2.7671 no . 3_557 H(8) H(10) 3.5068 no . 2_546 H(8) H(11) 3.1540 no . 2_546 H(9) C(4) 3.5708 no . 2_546 H(9) C(5) 3.5252 no . 2_546 H(9) C(6) 3.2049 no . 2_546 H(9) C(7) 2.9441 no . 2_546 H(9) C(8) 3.0305 no . 2_546 H(9) C(9) 3.3477 no . 2_546 H(9) H(5) 3.0263 no . 4_454 H(9) H(6) 3.4542 no . 3_657 H(9) H(6) 3.5361 no . 4_454 H(9) H(11) 3.2779 no . 2_546 H(9) H(12) 3.4207 no . 2_546 H(9) H(12) 3.3847 no . 4_454 H(10) O(2) 2.9490 no . 2_546 H(10) N(2) 2.9336 no . 4_554 H(10) C(3) 3.5669 no . 2_556 H(10) C(11) 3.5632 no . 2_546 H(10) H(3) 2.5059 no . 4_554 H(10) H(4) 3.1700 no . 4_554 H(10) H(7) 2.8753 no . 2_556 H(10) H(8) 3.5068 no . 2_556 H(10) H(12) 3.1368 no . 4_454 H(11) O(1) 3.3867 no . 3_657 H(11) O(1) 3.0685 no . 4_554 H(11) O(2) 3.2957 no . 3_667 H(11) N(1) 2.7226 no . 4_554 H(11) N(2) 3.4415 no . 4_554 H(11) C(10) 2.9917 no . 4_554 H(11) H(1) 2.5102 no . 4_554 H(11) H(2) 3.2398 no . 4_554 H(11) H(4) 3.4906 no . 4_554 H(11) H(5) 3.4175 no . 3_667 H(11) H(8) 3.1540 no . 2_556 H(11) H(9) 3.2779 no . 2_556 H(12) O(2) 2.7252 no . 3_667 H(12) C(1) 3.5531 no . 3_667 H(12) H(1) 3.4163 no . 4_554 H(12) H(5) 2.7433 no . 3_667 H(12) H(7) 2.9187 no . 3_657 H(12) H(9) 3.4207 no . 2_556 H(12) H(9) 3.3847 no . 4_555 H(12) H(10) 3.1368 no . 4_555 H(12) H(12) 3.4156 no . 3_667 #============================================================================== loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_D _geom_hbond_site_symmetry_H _geom_hbond_site_symmetry_A _geom_hbond_distance_DA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_angle_DHA _geom_hbond_publ_flag N(1) H(1) O(2) . . 2_547 2.974(2) 0.950 2.027 174.4 no N(1) H(2) O(1) . . 2_557 2.9555(18) 0.950 2.389 117.9 no N(2) H(3) O(2) . . 3_567 2.9599(17) 0.950 2.022 169.0 no N(2) H(4) O(1) . . 3_557 2.7948(15) 0.950 2.023 137.1 no data_030714__ _database_code_depnum_ccdc_archive 'CCDC 805787' #TrackingRef 'NaphHH.cif' _audit_creation_date 2010-12-24 _audit_creation_method 'by CrystalStructure 4.0' _audit_update_record ? #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C15 H14 N2 O2' _chemical_formula_moiety 'C15 H14 N2 O2' _chemical_formula_weight 254.29 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,1/2+Y,1/2-Z 3 -X,-Y,-Z 4 +X,1/2-Y,1/2+Z #------------------------------------------------------------------------------ _cell_length_a 11.91(4) _cell_length_b 7.938(5) _cell_length_c 13.481(11) _cell_angle_alpha 90.0000 _cell_angle_beta 107.32(4) _cell_angle_gamma 90.0000 _cell_volume 1217(4) _cell_formula_units_Z 4 _cell_measurement_reflns_used 49 _cell_measurement_theta_min 1.79 _cell_measurement_theta_max 27.10 _cell_measurement_temperature 153 #------------------------------------------------------------------------------ _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.200 _exptl_crystal_density_diffrn 1.388 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 536.00 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'REQAB (Rigaku, 1998)' _exptl_absorpt_correction_T_min 0.866 _exptl_absorpt_correction_T_max 0.981 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 153 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71070 _diffrn_measurement_device_type 'Rigaku Mercury70' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 7.314 _diffrn_reflns_number 7007 _diffrn_reflns_av_R_equivalents 0.0582 _diffrn_reflns_theta_max 27.10 _diffrn_reflns_theta_full 27.10 _diffrn_measured_fraction_theta_max 0.986 _diffrn_measured_fraction_theta_full 0.986 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 17 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_decay_% ? #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 2645 _reflns_number_gt 1508 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0756 _refine_ls_wR_factor_ref 0.2130 _refine_ls_number_restraints ? _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 2645 _refine_ls_number_parameters 186 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[0.0026Fo^2^ + 1.0000\s(Fo^2^)]/(4Fo^2^)' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_diff_density_max 0.791 _refine_diff_density_min -0.757 _refine_ls_extinction_method none _refine_ls_extinction_coef ? 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 for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.0000 0.0000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; N N 0.0061 0.0033 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.0106 0.0060 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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 0.62133(19) 0.4591(3) 0.42990(16) 0.0295(7) Uani 1.0 4 d . . . O2 O 0.5128(2) -0.0443(3) 0.36009(16) 0.0325(7) Uani 1.0 4 d . . . N1 N 0.5206(3) 0.2836(3) 0.5009(2) 0.0293(8) Uani 1.0 4 d . . . N2 N 0.5504(3) 0.1356(3) 0.2467(2) 0.0314(8) Uani 1.0 4 d . . . C1 C 0.7126(3) 0.0399(4) 0.5218(3) 0.0243(9) Uani 1.0 4 d . . . C2 C 0.6651(3) 0.1610(4) 0.4280(3) 0.0231(9) Uani 1.0 4 d . . . C3 C 0.7757(3) 0.2132(4) 0.3980(3) 0.0253(9) Uani 1.0 4 d . . . C4 C 0.8737(3) 0.1944(4) 0.4967(3) 0.0248(9) Uani 1.0 4 d . . . C5 C 0.9874(3) 0.2508(4) 0.5214(3) 0.0272(10) Uani 1.0 4 d . . . C6 C 1.0678(3) 0.2124(4) 0.6196(3) 0.0280(9) Uani 1.0 4 d . . . C7 C 1.1860(3) 0.2705(4) 0.6493(3) 0.0333(10) Uani 1.0 4 d . . . C8 C 1.2612(3) 0.2311(5) 0.7436(3) 0.0371(11) Uani 1.0 4 d . . . C9 C 1.2226(3) 0.1314(5) 0.8128(3) 0.0382(11) Uani 1.0 4 d . . . C10 C 1.1110(3) 0.0734(4) 0.7879(3) 0.0325(10) Uani 1.0 4 d . . . C11 C 1.0293(3) 0.1134(4) 0.6910(3) 0.0262(9) Uani 1.0 4 d . . . C12 C 0.9116(3) 0.0570(4) 0.6630(3) 0.0269(9) Uani 1.0 4 d . . . C13 C 0.8370(3) 0.0962(4) 0.5688(3) 0.0241(9) Uani 1.0 4 d . . . C14 C 0.6022(3) 0.3153(4) 0.4550(3) 0.0231(9) Uani 1.0 4 d . . . C15 C 0.5704(3) 0.0746(4) 0.3415(3) 0.0227(9) Uani 1.0 4 d . . . H1 H 0.4754 0.3712 0.5146 0.0364 Uiso 1.0 4 calc R . . H2 H 0.5081 0.1738 0.5192 0.0365 Uiso 1.0 4 calc R . . H3 H 0.4915 0.0893 0.1919 0.0368 Uiso 1.0 4 calc R . . H4 H 0.5955 0.2246 0.2347 0.0369 Uiso 1.0 4 calc R . . H5 H 0.6696 0.0505 0.5723 0.0298 Uiso 1.0 4 calc R . . H6 H 0.7121 -0.0769 0.5005 0.0296 Uiso 1.0 4 calc R . . H7 H 0.7896 0.1399 0.3453 0.0313 Uiso 1.0 4 calc R . . H8 H 0.7712 0.3291 0.3744 0.0313 Uiso 1.0 4 calc R . . H9 H 1.0120 0.3147 0.4739 0.0340 Uiso 1.0 4 calc R . . H10 H 1.2117 0.3349 0.6027 0.0404 Uiso 1.0 4 calc R . . H11 H 1.3376 0.2726 0.7632 0.0445 Uiso 1.0 4 calc R . . H12 H 1.2756 0.1021 0.8764 0.0437 Uiso 1.0 4 calc R . . H13 H 1.0874 0.0077 0.8352 0.0384 Uiso 1.0 4 calc R . . H14 H 0.8858 -0.0091 0.7088 0.0325 Uiso 1.0 4 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 0.0329(14) 0.0243(12) 0.0326(14) 0.0002(10) 0.0119(11) 0.0026(10) O2 0.0374(15) 0.0290(12) 0.0303(14) -0.0088(11) 0.0087(11) 0.0004(10) N1 0.0333(17) 0.0208(13) 0.0367(17) 0.0018(12) 0.0147(14) 0.0022(12) N2 0.0341(18) 0.0311(15) 0.0265(16) -0.0071(12) 0.0052(13) 0.0022(12) C1 0.0237(17) 0.0247(16) 0.0259(18) 0.0005(13) 0.0093(14) 0.0042(13) C2 0.0253(18) 0.0230(15) 0.0214(17) -0.0003(13) 0.0074(14) 0.0004(13) C3 0.0295(19) 0.0241(15) 0.0250(18) 0.0019(13) 0.0122(15) 0.0032(13) C4 0.0246(19) 0.0233(16) 0.0277(18) -0.0001(13) 0.0095(15) -0.0001(13) C5 0.032(2) 0.0251(16) 0.0278(19) -0.0010(14) 0.0143(16) -0.0013(14) C6 0.028(2) 0.0266(16) 0.0326(19) -0.0041(14) 0.0131(16) -0.0066(14) C7 0.031(2) 0.0318(18) 0.039(3) -0.0023(15) 0.0125(17) -0.0078(15) C8 0.023(2) 0.042(2) 0.046(3) -0.0036(15) 0.0097(18) -0.0092(17) C9 0.025(2) 0.046(2) 0.038(3) 0.0029(16) 0.0014(17) -0.0091(17) C10 0.031(2) 0.0309(17) 0.035(2) 0.0044(15) 0.0084(16) -0.0006(15) C11 0.0235(19) 0.0278(17) 0.0289(18) 0.0034(13) 0.0104(15) -0.0019(14) C12 0.0271(19) 0.0250(16) 0.0294(19) 0.0014(13) 0.0097(15) 0.0048(14) C13 0.0272(19) 0.0208(15) 0.0249(18) 0.0016(13) 0.0086(14) 0.0003(13) C14 0.0248(18) 0.0242(16) 0.0173(17) 0.0004(13) 0.0017(14) 0.0012(13) C15 0.0254(18) 0.0188(15) 0.0244(18) 0.0041(13) 0.0081(14) 0.0020(13) #============================================================================== _computing_data_collection 'CrystalClear (Rigaku Corp., 2000)' _computing_cell_refinement CrystalClear _computing_data_reduction CrystalClear _computing_structure_solution SIR97 _computing_structure_refinement 'CRYSTALS (Carruthers, et al., 1999)' _computing_publication_material 'CrystalStructure 4.0 (Rigaku, 2010)' _computing_molecular_graphics 'CrystalStructure 4.0' #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 O1 C14 1.231(4) yes . . O2 C15 1.235(4) yes . . N1 C14 1.322(6) yes . . N2 C15 1.321(5) yes . . C1 C2 1.555(4) yes . . C1 C13 1.496(6) yes . . C2 C3 1.545(6) yes . . C2 C14 1.535(5) yes . . C2 C15 1.523(5) yes . . C3 C4 1.493(5) yes . . C4 C5 1.370(6) yes . . C4 C13 1.414(5) yes . . C5 C6 1.416(5) yes . . C6 C7 1.421(6) yes . . C6 C11 1.420(5) yes . . C7 C8 1.356(5) yes . . C8 C9 1.401(6) yes . . C9 C10 1.351(6) yes . . C10 C11 1.413(5) yes . . C11 C12 1.412(6) yes . . C12 C13 1.351(4) yes . . N1 H1 0.930 no . . N1 H2 0.930 no . . N2 H3 0.930 no . . N2 H4 0.930 no . . C1 H5 0.970 no . . C1 H6 0.970 no . . C3 H7 0.970 no . . C3 H8 0.970 no . . C5 H9 0.930 no . . C7 H10 0.930 no . . C8 H11 0.930 no . . C9 H12 0.930 no . . C10 H13 0.930 no . . C12 H14 0.930 no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 C2 C1 C13 103.6(3) yes . . . C1 C2 C3 104.3(3) yes . . . C1 C2 C14 112.7(3) yes . . . C1 C2 C15 110.6(3) yes . . . C3 C2 C14 111.3(3) yes . . . C3 C2 C15 114.5(3) yes . . . C14 C2 C15 103.8(3) yes . . . C2 C3 C4 104.0(3) yes . . . C3 C4 C5 129.7(4) yes . . . C3 C4 C13 110.4(3) yes . . . C5 C4 C13 119.9(3) yes . . . C4 C5 C6 120.1(4) yes . . . C5 C6 C7 122.0(4) yes . . . C5 C6 C11 119.2(4) yes . . . C7 C6 C11 118.7(3) yes . . . C6 C7 C8 120.8(4) yes . . . C7 C8 C9 119.9(4) yes . . . C8 C9 C10 121.3(3) yes . . . C9 C10 C11 120.6(4) yes . . . C6 C11 C10 118.6(4) yes . . . C6 C11 C12 119.3(3) yes . . . C10 C11 C12 122.1(4) yes . . . C11 C12 C13 120.1(4) yes . . . C1 C13 C4 110.0(3) yes . . . C1 C13 C12 128.4(3) yes . . . C4 C13 C12 121.5(4) yes . . . O1 C14 N1 121.8(3) yes . . . O1 C14 C2 122.1(4) yes . . . N1 C14 C2 116.0(3) yes . . . O2 C15 N2 121.7(3) yes . . . O2 C15 C2 121.2(3) yes . . . N2 C15 C2 117.0(3) yes . . . C14 N1 H1 119.982 no . . . C14 N1 H2 120.021 no . . . H1 N1 H2 119.996 no . . . C15 N2 H3 120.006 no . . . C15 N2 H4 119.991 no . . . H3 N2 H4 120.003 no . . . C2 C1 H5 112.141 no . . . C2 C1 H6 112.376 no . . . C13 C1 H5 109.923 no . . . C13 C1 H6 109.235 no . . . H5 C1 H6 109.400 no . . . C2 C3 H7 112.072 no . . . C2 C3 H8 111.872 no . . . C4 C3 H7 109.513 no . . . C4 C3 H8 109.832 no . . . H7 C3 H8 109.428 no . . . C4 C5 H9 120.090 no . . . C6 C5 H9 119.841 no . . . C6 C7 H10 119.081 no . . . C8 C7 H10 120.116 no . . . C7 C8 H11 120.089 no . . . C9 C8 H11 119.957 no . . . C8 C9 H12 119.243 no . . . C10 C9 H12 119.425 no . . . C9 C10 H13 119.735 no . . . C11 C10 H13 119.614 no . . . C11 C12 H14 119.972 no . . . C13 C12 H14 119.942 no . . . 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_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C2 C1 C13 C4 -17.8(3) no . . . . C2 C1 C13 C12 165.8(3) no . . . . C13 C1 C2 C3 26.8(3) no . . . . C13 C1 C2 C14 -94.0(3) no . . . . C13 C1 C2 C15 150.3(3) no . . . . C1 C2 C3 C4 -26.1(3) no . . . . C1 C2 C14 O1 133.7(3) no . . . . C1 C2 C14 N1 -50.6(3) no . . . . C1 C2 C15 O2 24.3(4) no . . . . C1 C2 C15 N2 -157.7(3) no . . . . C3 C2 C14 O1 17.0(4) no . . . . C3 C2 C14 N1 -167.3(2) no . . . . C14 C2 C3 C4 95.6(3) no . . . . C3 C2 C15 O2 141.7(3) no . . . . C3 C2 C15 N2 -40.2(4) no . . . . C15 C2 C3 C4 -147.1(2) no . . . . C14 C2 C15 O2 -96.7(4) no . . . . C14 C2 C15 N2 81.3(4) no . . . . C15 C2 C14 O1 -106.7(3) no . . . . C15 C2 C14 N1 69.0(3) no . . . . C2 C3 C4 C5 -167.0(3) no . . . . C2 C3 C4 C13 16.0(3) no . . . . C3 C4 C5 C6 -177.4(3) no . . . . C3 C4 C13 C1 1.2(4) no . . . . C3 C4 C13 C12 177.9(3) no . . . . C5 C4 C13 C1 -176.1(3) no . . . . C5 C4 C13 C12 0.5(5) no . . . . C13 C4 C5 C6 -0.7(5) no . . . . C4 C5 C6 C7 -178.9(3) no . . . . C4 C5 C6 C11 0.7(5) no . . . . C5 C6 C7 C8 -179.7(3) no . . . . C5 C6 C11 C10 178.9(3) no . . . . C5 C6 C11 C12 -0.6(5) no . . . . C7 C6 C11 C10 -1.5(5) no . . . . C7 C6 C11 C12 179.1(3) no . . . . C11 C6 C7 C8 0.6(5) no . . . . C6 C7 C8 C9 0.2(5) no . . . . C7 C8 C9 C10 -0.2(6) no . . . . C8 C9 C10 C11 -0.7(6) no . . . . C9 C10 C11 C6 1.5(5) no . . . . C9 C10 C11 C12 -179.1(3) no . . . . C6 C11 C12 C13 0.4(5) no . . . . C10 C11 C12 C13 -179.0(3) no . . . . C11 C12 C13 C1 175.6(3) no . . . . C11 C12 C13 C4 -0.4(5) no . . . . #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #============================================================================== data_18Naph1 _database_code_depnum_ccdc_archive 'CCDC 875049' #TrackingRef '18Naph_diamide2.cif' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C15 H14 N2 O2' _chemical_formula_moiety 'C15 H14 N2 O2' _chemical_formula_weight 254.29 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 1/2-X,1/2+Y,1/2-Z 3 -X,-Y,-Z 4 1/2+X,1/2-Y,1/2+Z #------------------------------------------------------------------------------ _cell_length_a 11.4332(6) _cell_length_b 8.6325(5) _cell_length_c 13.0666(7) _cell_angle_alpha 90.0000 _cell_angle_beta 109.3700(10) _cell_angle_gamma 90.0000 _cell_volume 1216.64(12) _cell_formula_units_Z 4 _cell_measurement_reflns_used 1972 _cell_measurement_theta_min 2.88 _cell_measurement_theta_max 27.03 _cell_measurement_temperature 153 #------------------------------------------------------------------------------ _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.200 _exptl_crystal_density_diffrn 1.388 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 536.00 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9815 _exptl_absorpt_correction_T_max 0.9815 _exptl_absorpt_process_details ; SADABS Sheldrick 1996 ; _exptl_special_details ; ? ; #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 153 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71069 _diffrn_measurement_device_type 'Unknown CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 7164 _diffrn_reflns_av_R_equivalents 0.0240 _diffrn_reflns_theta_max 27.47 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_max 0.981 _diffrn_measured_fraction_theta_full 0.981 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_decay_% ? #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 2735 _reflns_number_gt 2200 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0442 _refine_ls_wR_factor_ref 0.1262 _refine_ls_number_restraints ? _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 2735 _refine_ls_number_parameters 186 _refine_ls_goodness_of_fit_ref 1.203 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[0.0010Fo^2^ + 1.0000\s(Fo^2^)]/(4Fo^2^)' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_diff_density_max 0.408 _refine_diff_density_min -0.265 _refine_ls_extinction_method none _refine_ls_extinction_coef ? 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 for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.0000 0.0000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; N N 0.0061 0.0033 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.0106 0.0060 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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 0.84601(10) 0.06012(11) 0.92556(9) 0.0293(3) Uani 1.0 4 d . . . O2 O 0.86566(9) 0.52501(11) 0.83694(8) 0.0223(3) Uani 1.0 4 d . . . N1 N 0.99168(11) 0.20949(14) 1.04050(10) 0.0252(4) Uani 1.0 4 d . . . N2 N 0.77810(12) 0.31274(14) 0.74311(10) 0.0236(4) Uani 1.0 4 d . . . C1 C 0.65836(13) 0.26881(16) 0.90665(12) 0.0195(4) Uani 1.0 4 d . . . C2 C 0.79235(12) 0.32765(16) 0.93371(11) 0.0176(4) Uani 1.0 4 d . . . C3 C 0.81452(13) 0.45169(16) 1.02211(11) 0.0198(4) Uani 1.0 4 d . . . C4 C 0.71965(14) 0.57992(16) 0.99032(11) 0.0207(4) Uani 1.0 4 d . . . C5 C 0.74814(15) 0.72692(17) 1.03122(12) 0.0246(4) Uani 1.0 4 d . . . C6 C 0.65993(16) 0.84746(18) 1.00088(13) 0.0285(5) Uani 1.0 4 d . . . C7 C 0.54433(15) 0.82053(18) 0.92911(13) 0.0288(5) Uani 1.0 4 d . . . C8 C 0.51006(14) 0.67175(17) 0.88478(13) 0.0248(4) Uani 1.0 4 d . . . C9 C 0.39113(15) 0.63939(19) 0.81012(14) 0.0313(5) Uani 1.0 4 d . . . C10 C 0.36132(15) 0.4938(2) 0.76925(14) 0.0339(5) Uani 1.0 4 d . . . C11 C 0.44873(15) 0.37268(19) 0.79979(13) 0.0274(5) Uani 1.0 4 d . . . C12 C 0.56542(13) 0.39851(16) 0.87181(11) 0.0204(4) Uani 1.0 4 d . . . C13 C 0.59836(13) 0.54899(17) 0.91616(11) 0.0205(4) Uani 1.0 4 d . . . C14 C 0.88038(13) 0.18707(15) 0.96792(11) 0.0185(4) Uani 1.0 4 d . . . C15 C 0.81465(12) 0.39756(15) 0.83275(11) 0.0171(4) Uani 1.0 4 d . . . H1 H 1.0473 0.1275 1.0614 0.0279 Uiso 1.0 4 calc R . . H2 H 1.0141 0.3072 1.0707 0.0280 Uiso 1.0 4 calc R . . H3 H 0.7908 0.3487 0.6805 0.0297 Uiso 1.0 4 calc R . . H4 H 0.7399 0.2175 0.7427 0.0296 Uiso 1.0 4 calc R . . H5 H 0.6403 0.1946 0.8477 0.0235 Uiso 1.0 4 calc R . . H6 H 0.6483 0.2196 0.9699 0.0234 Uiso 1.0 4 calc R . . H7 H 0.8101 0.4042 1.0880 0.0234 Uiso 1.0 4 calc R . . H8 H 0.8961 0.4967 1.0360 0.0233 Uiso 1.0 4 calc R . . H9 H 0.8270 0.7465 1.0799 0.0309 Uiso 1.0 4 calc R . . H10 H 0.6809 0.9459 1.0302 0.0370 Uiso 1.0 4 calc R . . H11 H 0.4873 0.9011 0.9086 0.0380 Uiso 1.0 4 calc R . . H12 H 0.3329 0.7185 0.7887 0.0386 Uiso 1.0 4 calc R . . H13 H 0.2826 0.4746 0.7204 0.0393 Uiso 1.0 4 calc R . . H14 H 0.4273 0.2740 0.7712 0.0329 Uiso 1.0 4 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 0.0252(6) 0.0145(6) 0.0402(7) 0.0028(5) 0.0001(5) -0.0055(5) O2 0.0257(6) 0.0143(6) 0.0259(6) -0.0037(4) 0.0072(5) -0.0002(4) N1 0.0208(7) 0.0144(7) 0.0339(8) 0.0036(5) 0.0001(6) -0.0029(6) N2 0.0325(8) 0.0181(7) 0.0213(7) -0.0052(6) 0.0102(6) -0.0014(5) C1 0.0195(8) 0.0155(8) 0.0247(8) 0.0008(6) 0.0090(6) 0.0007(6) C2 0.0177(8) 0.0134(7) 0.0208(8) 0.0015(6) 0.0053(6) -0.0002(6) C3 0.0230(8) 0.0163(8) 0.0190(7) 0.0022(6) 0.0058(6) -0.0007(6) C4 0.0267(8) 0.0171(8) 0.0219(7) 0.0029(6) 0.0127(6) 0.0015(6) C5 0.0322(9) 0.0196(8) 0.0252(8) 0.0021(6) 0.0135(7) -0.0012(6) C6 0.0427(10) 0.0163(8) 0.0336(9) 0.0036(7) 0.0222(8) -0.0014(7) C7 0.0374(10) 0.0199(8) 0.0377(9) 0.0118(7) 0.0237(8) 0.0079(7) C8 0.0270(9) 0.0233(8) 0.0292(8) 0.0062(7) 0.0162(7) 0.0075(7) C9 0.0255(9) 0.0313(10) 0.0402(10) 0.0116(7) 0.0151(8) 0.0136(8) C10 0.0204(8) 0.0393(11) 0.0387(10) 0.0027(7) 0.0053(7) 0.0080(8) C11 0.0242(8) 0.0242(9) 0.0339(9) -0.0007(6) 0.0099(7) 0.0024(7) C12 0.0204(8) 0.0188(8) 0.0249(8) 0.0022(6) 0.0111(6) 0.0034(6) C13 0.0234(8) 0.0191(8) 0.0231(7) 0.0045(6) 0.0132(6) 0.0044(6) C14 0.0204(7) 0.0143(7) 0.0215(7) 0.0017(6) 0.0078(6) 0.0016(6) C15 0.0129(7) 0.0139(7) 0.0229(7) 0.0030(5) 0.0037(6) 0.0009(6) #============================================================================== _computing_data_collection 'SMART (Bruker AXS, 2000)' _computing_cell_refinement 'SMART (Bruker AXS, 2000)' _computing_data_reduction 'SAINT (Bruker AXS, 2003)' _computing_structure_solution SIR97 _computing_structure_refinement 'CRYSTALS (Carruthers, et al., 1999)' _computing_publication_material 'CrystalStructure 4.0 (Rigaku, 2010)' _computing_molecular_graphics 'CrystalStructure 4.0' #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 O1 C14 1.2319(16) yes . . O2 C15 1.2379(17) yes . . N1 C14 1.3250(17) yes . . N2 C15 1.3259(18) yes . . C1 C2 1.540(2) yes . . C1 C12 1.506(2) yes . . C2 C3 1.533(2) yes . . C2 C14 1.5450(19) yes . . C2 C15 1.547(3) yes . . C3 C4 1.508(2) yes . . C4 C5 1.374(2) yes . . C4 C13 1.4290(19) yes . . C5 C6 1.411(3) yes . . C6 C7 1.363(2) yes . . C7 C8 1.410(3) yes . . C8 C9 1.414(2) yes . . C8 C13 1.427(2) yes . . C9 C10 1.364(3) yes . . C10 C11 1.410(3) yes . . C11 C12 1.3720(19) yes . . C12 C13 1.421(2) yes . . N1 H1 0.930 no . . N1 H2 0.930 no . . N2 H3 0.930 no . . N2 H4 0.930 no . . C1 H5 0.970 no . . C1 H6 0.970 no . . C3 H7 0.970 no . . C3 H8 0.970 no . . C5 H9 0.930 no . . C6 H10 0.930 no . . C7 H11 0.930 no . . C9 H12 0.930 no . . C10 H13 0.930 no . . C11 H14 0.930 no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 C2 C1 C12 111.88(12) yes . . . C1 C2 C3 107.86(13) yes . . . C1 C2 C14 108.08(12) yes . . . C1 C2 C15 111.45(11) yes . . . C3 C2 C14 113.67(10) yes . . . C3 C2 C15 109.71(12) yes . . . C14 C2 C15 106.10(13) yes . . . C2 C3 C4 112.39(10) yes . . . C3 C4 C5 120.98(13) yes . . . C3 C4 C13 119.81(12) yes . . . C5 C4 C13 119.21(14) yes . . . C4 C5 C6 121.11(14) yes . . . C5 C6 C7 120.46(15) yes . . . C6 C7 C8 120.79(15) yes . . . C7 C8 C9 122.42(14) yes . . . C7 C8 C13 119.00(13) yes . . . C9 C8 C13 118.59(14) yes . . . C8 C9 C10 120.70(15) yes . . . C9 C10 C11 120.74(14) yes . . . C10 C11 C12 120.69(15) yes . . . C1 C12 C11 120.96(13) yes . . . C1 C12 C13 119.41(11) yes . . . C11 C12 C13 119.61(13) yes . . . C4 C13 C8 119.41(13) yes . . . C4 C13 C12 120.90(13) yes . . . C8 C13 C12 119.68(12) yes . . . O1 C14 N1 122.62(13) yes . . . O1 C14 C2 119.25(11) yes . . . N1 C14 C2 118.11(12) yes . . . O2 C15 N2 122.39(15) yes . . . O2 C15 C2 121.17(12) yes . . . N2 C15 C2 116.43(12) yes . . . C14 N1 H1 119.997 no . . . C14 N1 H2 120.004 no . . . H1 N1 H2 119.999 no . . . C15 N2 H3 119.781 no . . . C15 N2 H4 120.216 no . . . H3 N2 H4 120.003 no . . . C2 C1 H5 109.496 no . . . C2 C1 H6 109.815 no . . . C12 C1 H5 107.943 no . . . C12 C1 H6 108.193 no . . . H5 C1 H6 109.467 no . . . C2 C3 H7 109.246 no . . . C2 C3 H8 109.224 no . . . C4 C3 H7 108.041 no . . . C4 C3 H8 108.416 no . . . H7 C3 H8 109.483 no . . . C4 C5 H9 118.999 no . . . C6 C5 H9 119.887 no . . . C5 C6 H10 119.665 no . . . C7 C6 H10 119.872 no . . . C6 C7 H11 119.857 no . . . C8 C7 H11 119.352 no . . . C8 C9 H12 119.424 no . . . C10 C9 H12 119.875 no . . . C9 C10 H13 119.537 no . . . C11 C10 H13 119.723 no . . . C10 C11 H14 119.893 no . . . C12 C11 H14 119.417 no . . . 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_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C2 C1 C12 C11 149.63(13) no . . . . C2 C1 C12 C13 -31.80(19) no . . . . C12 C1 C2 C3 56.94(15) no . . . . C12 C1 C2 C14 -179.77(11) no . . . . C12 C1 C2 C15 -63.55(16) no . . . . C1 C2 C3 C4 -54.76(15) no . . . . C1 C2 C14 O1 33.31(19) no . . . . C1 C2 C14 N1 -148.19(13) no . . . . C1 C2 C15 O2 131.95(12) no . . . . C1 C2 C15 N2 -49.08(16) no . . . . C3 C2 C14 O1 153.00(14) no . . . . C3 C2 C14 N1 -28.5(2) no . . . . C14 C2 C3 C4 -174.58(12) no . . . . C3 C2 C15 O2 12.56(17) no . . . . C3 C2 C15 N2 -168.47(10) no . . . . C15 C2 C3 C4 66.81(14) no . . . . C14 C2 C15 O2 -110.63(13) no . . . . C14 C2 C15 N2 68.35(13) no . . . . C15 C2 C14 O1 -86.35(16) no . . . . C15 C2 C14 N1 92.16(14) no . . . . C2 C3 C4 C5 -152.15(13) no . . . . C2 C3 C4 C13 27.5(2) no . . . . C3 C4 C5 C6 179.43(14) no . . . . C3 C4 C13 C8 -178.68(13) no . . . . C3 C4 C13 C12 0.1(3) no . . . . C5 C4 C13 C8 1.0(3) no . . . . C5 C4 C13 C12 179.81(14) no . . . . C13 C4 C5 C6 -0.3(3) no . . . . C4 C5 C6 C7 -0.6(3) no . . . . C5 C6 C7 C8 0.7(3) no . . . . C6 C7 C8 C9 -179.97(16) no . . . . C6 C7 C8 C13 0.0(3) no . . . . C7 C8 C9 C10 -179.81(17) no . . . . C7 C8 C13 C4 -0.9(3) no . . . . C7 C8 C13 C12 -179.71(15) no . . . . C9 C8 C13 C4 179.09(15) no . . . . C9 C8 C13 C12 0.3(3) no . . . . C13 C8 C9 C10 0.2(3) no . . . . C8 C9 C10 C11 -0.6(3) no . . . . C9 C10 C11 C12 0.4(3) no . . . . C10 C11 C12 C1 178.66(15) no . . . . C10 C11 C12 C13 0.1(3) no . . . . C1 C12 C13 C4 2.2(3) no . . . . C1 C12 C13 C8 -179.01(13) no . . . . C11 C12 C13 C4 -179.22(15) no . . . . C11 C12 C13 C8 -0.4(3) no . . . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 O1 N2 3.1327(16) no . . O1 C1 2.7491(19) no . . O1 C15 3.1299(17) no . . O2 C1 3.574(2) no . . O2 C3 2.745(2) no . . O2 C4 3.041(2) no . . O2 C13 3.543(2) no . . O2 C14 3.3581(17) no . . N1 C3 2.8651(19) no . . N1 C15 3.2337(17) no . . N2 C1 2.920(3) no . . N2 C12 3.464(3) no . . N2 C14 2.9824(18) no . . C1 C4 2.897(2) no . . C2 C13 2.878(2) no . . C3 C12 2.9101(18) no . . C4 C7 2.812(3) no . . C4 C15 3.063(3) no . . C5 C8 2.800(2) no . . C6 C13 2.800(2) no . . C8 C11 2.806(3) no . . C9 C12 2.807(3) no . . C10 C13 2.794(2) no . . C12 C15 3.057(3) no . . C13 C15 3.286(3) no . . O1 O1 3.5661(15) no . 3_757 O1 O2 3.4939(14) no . 2_646 O1 N1 2.9174(16) no . 3_757 O1 N2 3.0589(16) no . 2_646 O1 C5 3.529(2) no . 1_545 O1 C6 3.202(3) no . 1_545 O1 C15 3.5529(17) no . 2_646 O2 O1 3.4939(14) no . 2_656 O2 N1 2.9572(15) no . 3_767 O2 N2 2.9706(16) no . 2_656 O2 C3 3.5122(17) no . 3_767 N1 O1 2.9174(16) no . 3_757 N1 O2 2.9572(15) no . 3_767 N1 N2 3.4668(16) no . 4_555 N1 C5 3.446(3) no . 3_767 N2 O1 3.0589(16) no . 2_656 N2 O2 2.9706(16) no . 2_646 N2 N1 3.4668(16) no . 4_454 N2 C5 3.574(2) no . 2_646 N2 C6 3.501(3) no . 2_646 N2 C7 3.496(3) no . 2_646 N2 C8 3.581(3) no . 2_646 C3 O2 3.5122(17) no . 3_767 C5 O1 3.529(2) no . 1_565 C5 N1 3.446(3) no . 3_767 C5 N2 3.574(2) no . 2_656 C6 O1 3.202(3) no . 1_565 C6 N2 3.501(3) no . 2_656 C7 N2 3.496(3) no . 2_656 C8 N2 3.581(3) no . 2_656 C15 O1 3.5529(17) no . 2_656 O1 H1 2.4649 no . . O1 H2 3.0691 no . . O1 H4 2.6653 no . . O1 H5 2.5152 no . . O1 H6 2.8652 no . . O2 H2 3.5080 no . . O2 H3 2.4625 no . . O2 H4 3.0750 no . . O2 H8 2.5189 no . . N1 H7 2.8945 no . . N1 H8 2.7028 no . . N2 H5 2.6112 no . . C1 H4 2.6423 no . . C1 H7 2.6953 no . . C1 H8 3.3266 no . . C1 H14 2.6480 no . . C2 H1 3.3227 no . . C2 H2 2.5792 no . . C2 H3 3.3072 no . . C2 H4 2.5497 no . . C3 H2 2.4911 no . . C3 H5 3.3280 no . . C3 H6 2.6892 no . . C3 H9 2.6448 no . . C4 H6 3.2045 no . . C4 H10 3.2557 no . . C5 H7 2.9091 no . . C5 H8 2.5966 no . . C5 H11 3.2484 no . . C7 H9 3.2418 no . . C7 H12 2.6539 no . . C8 H10 3.2502 no . . C8 H13 3.2514 no . . C9 H11 2.6515 no . . C9 H14 3.2434 no . . C11 H5 2.5776 no . . C11 H6 2.9209 no . . C11 H12 3.2499 no . . C12 H4 3.3916 no . . C12 H7 3.2504 no . . C12 H13 3.2497 no . . C13 H5 3.2672 no . . C13 H6 2.9395 no . . C13 H7 2.9761 no . . C13 H8 3.2717 no . . C13 H9 3.2566 no . . C13 H11 3.2831 no . . C13 H12 3.2825 no . . C13 H14 3.2545 no . . C14 H4 2.8590 no . . C14 H5 2.6731 no . . C14 H6 2.6769 no . . C14 H7 2.7313 no . . C14 H8 2.8042 no . . C15 H2 3.2819 no . . C15 H5 2.7093 no . . C15 H6 3.3842 no . . C15 H7 3.3536 no . . C15 H8 2.6479 no . . H1 H8 3.5889 no . . H2 H7 2.5585 no . . H2 H8 2.0735 no . . H3 H5 3.4635 no . . H4 H5 2.0632 no . . H4 H6 3.4610 no . . H5 H7 3.5860 no . . H5 H14 2.4053 no . . H6 H7 2.5395 no . . H6 H8 3.5876 no . . H6 H14 2.9994 no . . H7 H9 2.9649 no . . H8 H9 2.4294 no . . H9 H10 2.3350 no . . H10 H11 2.2894 no . . H11 H12 2.4941 no . . H12 H13 2.2854 no . . H13 H14 2.3343 no . . O1 H1 2.0005 no . 3_757 O1 H2 3.5441 no . 3_757 O1 H3 2.5022 no . 2_646 O1 H9 3.4258 no . 1_545 O1 H10 2.8485 no . 1_545 O2 H1 3.2979 no . 3_767 O2 H2 2.0846 no . 3_767 O2 H3 3.2850 no . 2_656 O2 H4 2.1137 no . 2_656 O2 H5 2.8035 no . 2_656 O2 H7 3.5592 no . 3_767 O2 H8 2.6859 no . 3_767 N1 H1 3.1687 no . 3_757 N1 H3 3.3387 no . 4_555 N1 H4 3.2341 no . 4_555 N1 H8 3.1509 no . 3_767 N1 H9 3.0138 no . 3_767 N1 H14 3.3350 no . 4_555 N2 H1 2.9513 no . 4_454 N2 H2 3.2783 no . 4_454 N2 H4 3.5086 no . 2_656 C1 H10 3.1886 no . 1_545 C3 H2 3.3494 no . 3_767 C4 H2 3.5300 no . 3_767 C4 H3 3.1948 no . 2_656 C4 H4 3.4390 no . 2_656 C5 H1 3.2235 no . 3_767 C5 H2 3.4131 no . 3_767 C5 H3 2.8537 no . 2_656 C5 H12 3.2123 no . 4_565 C5 H13 3.5012 no . 4_565 C6 H3 2.6120 no . 2_656 C6 H5 3.5689 no . 1_565 C6 H6 3.2348 no . 1_565 C6 H11 3.2036 no . 3_677 C6 H13 3.1439 no . 4_565 C6 H14 3.5961 no . 3_667 C7 H3 2.7306 no . 2_656 C7 H6 2.9390 no . 3_667 C7 H10 3.4485 no . 3_677 C7 H11 3.3029 no . 3_677 C8 H3 3.0878 no . 2_656 C8 H6 3.1690 no . 3_667 C9 H6 3.2870 no . 3_667 C9 H7 3.0392 no . 3_667 C9 H9 3.0157 no . 4_464 C9 H13 3.4568 no . 2_556 C10 H7 3.2430 no . 3_667 C10 H9 3.2644 no . 4_464 C10 H10 3.1638 no . 4_464 C10 H12 3.1679 no . 2_546 C11 H12 3.3173 no . 2_546 C13 H3 3.3105 no . 2_656 C13 H4 3.5196 no . 2_656 C14 H1 2.9008 no . 3_757 C14 H10 3.3804 no . 1_545 C15 H2 3.2069 no . 3_767 C15 H4 2.9293 no . 2_656 C15 H8 3.3093 no . 3_767 H1 O1 2.0005 no . 3_757 H1 O2 3.2979 no . 3_767 H1 N1 3.1687 no . 3_757 H1 N2 2.9513 no . 4_555 H1 C5 3.2235 no . 3_767 H1 C14 2.9008 no . 3_757 H1 H1 2.7275 no . 3_757 H1 H3 2.7096 no . 4_555 H1 H4 2.9651 no . 4_555 H1 H9 2.9016 no . 3_767 H1 H14 3.5521 no . 4_555 H2 O1 3.5441 no . 3_757 H2 O2 2.0846 no . 3_767 H2 N2 3.2783 no . 4_555 H2 C3 3.3494 no . 3_767 H2 C4 3.5300 no . 3_767 H2 C5 3.4131 no . 3_767 H2 C15 3.2069 no . 3_767 H2 H3 3.2968 no . 4_555 H2 H4 2.8133 no . 4_555 H2 H5 3.4237 no . 4_555 H2 H8 2.6101 no . 3_767 H2 H9 3.1239 no . 3_767 H2 H14 3.1729 no . 4_555 H3 O1 2.5022 no . 2_656 H3 O2 3.2850 no . 2_646 H3 N1 3.3387 no . 4_454 H3 C4 3.1948 no . 2_646 H3 C5 2.8537 no . 2_646 H3 C6 2.6120 no . 2_646 H3 C7 2.7306 no . 2_646 H3 C8 3.0878 no . 2_646 H3 C13 3.3105 no . 2_646 H3 H1 2.7096 no . 4_454 H3 H2 3.2968 no . 4_454 H3 H4 3.3908 no . 2_656 H3 H5 3.1405 no . 2_656 H3 H9 3.3368 no . 2_646 H3 H10 2.9964 no . 2_646 H3 H11 3.1557 no . 2_646 H4 O2 2.1137 no . 2_646 H4 N1 3.2341 no . 4_454 H4 N2 3.5086 no . 2_646 H4 C4 3.4390 no . 2_646 H4 C13 3.5196 no . 2_646 H4 C15 2.9293 no . 2_646 H4 H1 2.9651 no . 4_454 H4 H2 2.8133 no . 4_454 H4 H3 3.3908 no . 2_646 H5 O2 2.8035 no . 2_646 H5 C6 3.5689 no . 1_545 H5 H2 3.4237 no . 4_454 H5 H3 3.1405 no . 2_646 H5 H10 3.1265 no . 1_545 H5 H11 3.3221 no . 1_545 H6 C6 3.2348 no . 1_545 H6 C7 2.9390 no . 3_667 H6 C8 3.1690 no . 3_667 H6 C9 3.2870 no . 3_667 H6 H10 2.4792 no . 1_545 H6 H11 3.2574 no . 1_545 H6 H11 2.7638 no . 3_667 H6 H12 3.1347 no . 3_667 H6 H13 3.5413 no . 4_555 H7 O2 3.5592 no . 3_767 H7 C9 3.0392 no . 3_667 H7 C10 3.2430 no . 3_667 H7 H12 2.8522 no . 3_667 H7 H13 3.2007 no . 3_667 H7 H14 2.7866 no . 4_555 H8 O2 2.6859 no . 3_767 H8 N1 3.1509 no . 3_767 H8 C15 3.3093 no . 3_767 H8 H2 2.6101 no . 3_767 H8 H8 2.8319 no . 3_767 H9 O1 3.4258 no . 1_565 H9 N1 3.0138 no . 3_767 H9 C9 3.0157 no . 4_565 H9 C10 3.2644 no . 4_565 H9 H1 2.9016 no . 3_767 H9 H2 3.1239 no . 3_767 H9 H3 3.3368 no . 2_656 H9 H12 2.7237 no . 4_565 H9 H13 3.1691 no . 4_565 H10 O1 2.8485 no . 1_565 H10 C1 3.1886 no . 1_565 H10 C7 3.4485 no . 3_677 H10 C10 3.1638 no . 4_565 H10 C14 3.3804 no . 1_565 H10 H3 2.9964 no . 2_656 H10 H5 3.1265 no . 1_565 H10 H6 2.4792 no . 1_565 H10 H11 2.6655 no . 3_677 H10 H12 3.5429 no . 4_565 H10 H13 2.4663 no . 4_565 H11 C6 3.2036 no . 3_677 H11 C7 3.3029 no . 3_677 H11 H3 3.1557 no . 2_656 H11 H5 3.3221 no . 1_565 H11 H6 3.2574 no . 1_565 H11 H6 2.7638 no . 3_667 H11 H10 2.6655 no . 3_677 H11 H11 2.8710 no . 3_677 H11 H13 3.0516 no . 2_556 H12 C5 3.2123 no . 4_464 H12 C10 3.1679 no . 2_556 H12 C11 3.3173 no . 2_556 H12 H6 3.1347 no . 3_667 H12 H7 2.8522 no . 3_667 H12 H9 2.7237 no . 4_464 H12 H10 3.5429 no . 4_464 H12 H13 2.5568 no . 2_556 H12 H14 2.8540 no . 2_556 H13 C5 3.5012 no . 4_464 H13 C6 3.1439 no . 4_464 H13 C9 3.4568 no . 2_546 H13 H6 3.5413 no . 4_454 H13 H7 3.2007 no . 3_667 H13 H9 3.1691 no . 4_464 H13 H10 2.4663 no . 4_464 H13 H11 3.0516 no . 2_546 H13 H12 2.5568 no . 2_546 H13 H14 3.5530 no . 2_556 H14 N1 3.3350 no . 4_454 H14 C6 3.5961 no . 3_667 H14 H1 3.5521 no . 4_454 H14 H2 3.1729 no . 4_454 H14 H7 2.7866 no . 4_454 H14 H12 2.8540 no . 2_546 H14 H13 3.5530 no . 2_546 #============================================================================== loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_D _geom_hbond_site_symmetry_H _geom_hbond_site_symmetry_A _geom_hbond_distance_DA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_angle_DHA _geom_hbond_publ_flag N1 H1 O1 . . 3_757 2.9174(16) 0.930 2.001 168.4 no N1 H2 O2 . . 3_767 2.9572(15) 0.930 2.085 155.7 no N2 H3 O1 . . 2_656 3.0589(16) 0.930 2.502 118.6 no N2 H4 O2 . . 2_646 2.9706(16) 0.930 2.114 152.6 no data_IodoInd_Sh _database_code_depnum_ccdc_archive 'CCDC 875415' #TrackingRef 'IodoindeaneDiamide2.cif' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C11 H11 I N2 O2' _chemical_formula_moiety 'C11 H11 I N2 O2' _chemical_formula_weight 330.12 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,1/2+Y,1/2-Z 3 -X,-Y,-Z 4 +X,1/2-Y,1/2+Z #------------------------------------------------------------------------------ _cell_length_a 10.5351(16) _cell_length_b 8.1715(13) _cell_length_c 14.384(3) _cell_angle_alpha 90.0000 _cell_angle_beta 109.536(2) _cell_angle_gamma 90.0000 _cell_volume 1167.0(4) _cell_formula_units_Z 4 _cell_measurement_reflns_used 2359 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 25.44 _cell_measurement_temperature 153 #------------------------------------------------------------------------------ _exptl_crystal_description platelet _exptl_crystal_colour colorless _exptl_crystal_size_max 0.250 _exptl_crystal_size_mid 0.150 _exptl_crystal_size_min 0.050 _exptl_crystal_density_diffrn 1.879 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 640.00 _exptl_absorpt_coefficient_mu 2.732 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.5484 _exptl_absorpt_correction_T_max 0.8755 _exptl_absorpt_process_details ; SADABS Sheldrick 1996 ; _exptl_special_details ; ? ; #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 153 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_reflns_number 6758 _diffrn_reflns_av_R_equivalents 0.0199 _diffrn_reflns_theta_max 27.50 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_max 0.972 _diffrn_measured_fraction_theta_full 0.972 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_decay_% ? #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 2615 _reflns_number_gt 2180 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0453 _refine_ls_wR_factor_ref 0.1181 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 2615 _refine_ls_number_parameters 145 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0567P)^2^+3.9471P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_diff_density_max 2.660 _refine_diff_density_min -0.930 _refine_ls_extinction_method none _refine_ls_extinction_coef ? 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 for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.0000 0.0000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; N N 0.0061 0.0033 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.0106 0.0060 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; I I -0.4742 1.8119 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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 I1 I -0.21422(4) 0.11635(5) 0.16869(3) 0.04656(16) Uani 1.0 4 d . . . O1 O 0.3842(4) 0.4542(4) 0.5730(3) 0.0242(7) Uani 1.0 4 d . . . O2 O 0.4985(4) -0.0413(4) 0.6453(3) 0.0297(8) Uani 1.0 4 d . . . N1 N 0.4698(4) 0.2875(5) 0.4847(3) 0.0227(8) Uani 1.0 4 d . . . N2 N 0.4741(5) 0.1554(5) 0.7459(3) 0.0295(9) Uani 1.0 4 d . . . C1 C 0.2059(5) 0.2228(6) 0.5985(4) 0.0258(10) Uani 1.0 4 d . . . C2 C 0.3301(5) 0.1658(5) 0.5725(3) 0.0187(8) Uani 1.0 4 d . . . C3 C 0.2697(5) 0.0438(5) 0.4863(3) 0.0227(9) Uani 1.0 4 d . . . C4 C 0.1314(5) 0.1130(6) 0.4354(4) 0.0250(9) Uani 1.0 4 d . . . C5 C 0.0459(5) 0.0832(6) 0.3403(4) 0.0281(10) Uani 1.0 4 d . . . C6 C -0.0807(5) 0.1594(6) 0.3115(4) 0.0330(11) Uani 1.0 4 d . . . C7 C -0.1186(6) 0.2625(7) 0.3742(5) 0.0385(12) Uani 1.0 4 d . . . C8 C -0.0318(6) 0.2892(6) 0.4694(4) 0.0351(11) Uani 1.0 4 d . . . C9 C 0.0942(5) 0.2144(6) 0.4998(4) 0.0294(10) Uani 1.0 4 d . . . C10 C 0.3971(4) 0.3156(5) 0.5419(3) 0.0176(8) Uani 1.0 4 d . . . C11 C 0.4417(5) 0.0839(5) 0.6581(3) 0.0219(9) Uani 1.0 4 d . . . H1 H 0.5117 0.3688 0.4672 0.0272 Uiso 1.0 4 calc R . . H2 H 0.4765 0.1875 0.4642 0.0272 Uiso 1.0 4 calc R . . H3 H 0.5377 0.1132 0.7968 0.0354 Uiso 1.0 4 calc R . . H4 H 0.4321 0.2450 0.7533 0.0354 Uiso 1.0 4 calc R . . H5 H 0.1880 0.1488 0.6472 0.0309 Uiso 1.0 4 calc R . . H6 H 0.2180 0.3358 0.6250 0.0309 Uiso 1.0 4 calc R . . H7 H 0.3235 0.0413 0.4416 0.0272 Uiso 1.0 4 calc R . . H8 H 0.2646 -0.0681 0.5112 0.0272 Uiso 1.0 4 calc R . . H9 H 0.0718 0.0143 0.2966 0.0337 Uiso 1.0 4 calc R . . H10 H -0.2041 0.3147 0.3519 0.0462 Uiso 1.0 4 calc R . . H11 H -0.0579 0.3576 0.5132 0.0421 Uiso 1.0 4 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 I1 0.0361(3) 0.0556(3) 0.0396(3) -0.00983(16) 0.00160(15) 0.01402(17) O1 0.0370(18) 0.0143(14) 0.0259(15) -0.0060(13) 0.0168(14) -0.0031(12) O2 0.050(2) 0.0172(15) 0.0229(15) 0.0053(15) 0.0133(15) -0.0010(13) N1 0.037(2) 0.0128(16) 0.0227(17) -0.0056(15) 0.0151(16) -0.0005(14) N2 0.046(3) 0.0213(19) 0.0207(18) 0.0073(17) 0.0109(17) 0.0008(15) C1 0.037(3) 0.018(2) 0.030(3) -0.0047(18) 0.021(2) -0.0029(17) C2 0.027(2) 0.0121(17) 0.0187(18) -0.0038(16) 0.0104(16) -0.0007(15) C3 0.035(3) 0.0130(18) 0.023(2) -0.0069(18) 0.0131(18) -0.0021(16) C4 0.028(3) 0.018(2) 0.031(3) -0.0069(17) 0.0125(19) 0.0016(18) C5 0.034(3) 0.021(3) 0.031(3) -0.0067(18) 0.012(2) 0.0000(18) C6 0.030(3) 0.029(3) 0.038(3) -0.007(2) 0.009(2) 0.008(2) C7 0.032(3) 0.033(3) 0.054(4) -0.001(2) 0.018(3) 0.010(3) C8 0.036(3) 0.027(3) 0.051(3) -0.002(2) 0.025(3) 0.003(3) C9 0.035(3) 0.023(3) 0.038(3) -0.0052(19) 0.022(3) 0.0009(19) C10 0.024(2) 0.0153(18) 0.0117(16) -0.0035(16) 0.0040(15) -0.0013(15) C11 0.034(3) 0.017(2) 0.0182(19) -0.0074(17) 0.0140(18) 0.0019(15) #============================================================================== _computing_data_collection 'SMART (Bruker AXS, 2000)' _computing_cell_refinement 'SMART (Bruker AXS, 2000)' _computing_data_reduction 'SAINT (Bruker AXS, 2003)' _computing_structure_solution 'SIR2004 (Burla, et al., 2005)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_publication_material 'CrystalStructure 4.0 (Rigaku, 2010)' _computing_molecular_graphics 'CrystalStructure 4.0' #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 I1 C6 2.095(5) yes . . O1 C10 1.243(5) yes . . O2 C11 1.230(6) yes . . N1 C10 1.318(7) yes . . N2 C11 1.329(6) yes . . C1 C2 1.548(8) yes . . C1 C9 1.513(6) yes . . C2 C3 1.551(6) yes . . C2 C10 1.548(7) yes . . C2 C11 1.543(6) yes . . C3 C4 1.505(6) yes . . C4 C5 1.384(6) yes . . C4 C9 1.394(8) yes . . C5 C6 1.403(7) yes . . C6 C7 1.388(9) yes . . C7 C8 1.386(8) yes . . C8 C9 1.392(7) yes . . N1 H1 0.880 no . . N1 H2 0.880 no . . N2 H3 0.880 no . . N2 H4 0.880 no . . C1 H5 0.990 no . . C1 H6 0.990 no . . C3 H7 0.990 no . . C3 H8 0.990 no . . C5 H9 0.950 no . . C7 H10 0.950 no . . C8 H11 0.950 no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 C2 C1 C9 102.4(4) yes . . . C1 C2 C3 103.5(4) yes . . . C1 C2 C10 109.5(4) yes . . . C1 C2 C11 114.7(4) yes . . . C3 C2 C10 112.6(4) yes . . . C3 C2 C11 111.0(4) yes . . . C10 C2 C11 105.8(4) yes . . . C2 C3 C4 102.6(4) yes . . . C3 C4 C5 128.3(5) yes . . . C3 C4 C9 110.0(4) yes . . . C5 C4 C9 121.7(5) yes . . . C4 C5 C6 117.1(5) yes . . . I1 C6 C5 118.4(4) yes . . . I1 C6 C7 119.6(4) yes . . . C5 C6 C7 121.9(5) yes . . . C6 C7 C8 120.0(5) yes . . . C7 C8 C9 119.1(6) yes . . . C1 C9 C4 110.3(4) yes . . . C1 C9 C8 129.5(5) yes . . . C4 C9 C8 120.2(5) yes . . . O1 C10 N1 122.7(4) yes . . . O1 C10 C2 120.2(5) yes . . . N1 C10 C2 117.1(4) yes . . . O2 C11 N2 121.6(4) yes . . . O2 C11 C2 121.4(4) yes . . . N2 C11 C2 117.0(4) yes . . . C10 N1 H1 119.999 no . . . C10 N1 H2 119.999 no . . . H1 N1 H2 120.002 no . . . C11 N2 H3 120.002 no . . . C11 N2 H4 120.002 no . . . H3 N2 H4 119.996 no . . . C2 C1 H5 111.286 no . . . C2 C1 H6 111.286 no . . . C9 C1 H5 111.290 no . . . C9 C1 H6 111.286 no . . . H5 C1 H6 109.181 no . . . C2 C3 H7 111.237 no . . . C2 C3 H8 111.239 no . . . C4 C3 H7 111.235 no . . . C4 C3 H8 111.238 no . . . H7 C3 H8 109.146 no . . . C4 C5 H9 121.467 no . . . C6 C5 H9 121.470 no . . . C6 C7 H10 120.002 no . . . C8 C7 H10 120.007 no . . . C7 C8 H11 120.458 no . . . C9 C8 H11 120.461 no . . . 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_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C2 C1 C9 C4 19.6(5) no . . . . C2 C1 C9 C8 -161.2(5) no . . . . C9 C1 C2 C3 -31.3(4) no . . . . C9 C1 C2 C10 89.0(4) no . . . . C9 C1 C2 C11 -152.4(3) no . . . . C1 C2 C3 C4 32.0(4) no . . . . C1 C2 C10 O1 26.0(5) no . . . . C1 C2 C10 N1 -155.9(3) no . . . . C1 C2 C11 O2 136.4(5) no . . . . C1 C2 C11 N2 -44.0(5) no . . . . C3 C2 C10 O1 140.5(4) no . . . . C3 C2 C10 N1 -41.4(5) no . . . . C10 C2 C3 C4 -86.2(4) no . . . . C3 C2 C11 O2 19.6(7) no . . . . C3 C2 C11 N2 -160.8(4) no . . . . C11 C2 C3 C4 155.5(4) no . . . . C10 C2 C11 O2 -102.8(5) no . . . . C10 C2 C11 N2 76.7(5) no . . . . C11 C2 C10 O1 -98.1(4) no . . . . C11 C2 C10 N1 80.0(4) no . . . . C2 C3 C4 C5 160.9(5) no . . . . C2 C3 C4 C9 -20.9(5) no . . . . C3 C4 C5 C6 177.9(4) no . . . . C3 C4 C9 C1 0.9(6) no . . . . C3 C4 C9 C8 -178.4(4) no . . . . C5 C4 C9 C1 179.2(4) no . . . . C5 C4 C9 C8 -0.1(8) no . . . . C9 C4 C5 C6 -0.2(7) no . . . . C4 C5 C6 I1 -179.5(4) no . . . . C4 C5 C6 C7 1.1(8) no . . . . I1 C6 C7 C8 178.8(4) no . . . . C5 C6 C7 C8 -1.7(9) no . . . . C6 C7 C8 C9 1.4(9) no . . . . C7 C8 C9 C1 -179.7(5) no . . . . C7 C8 C9 C4 -0.6(8) no . . . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 O1 N2 3.387(5) no . . O1 C1 2.774(6) no . . O1 C9 3.483(6) no . . O1 C11 3.244(5) no . . O2 N1 3.490(5) no . . O2 C3 2.799(5) no . . O2 C10 3.286(5) no . . N1 C3 2.906(6) no . . N1 C11 3.093(6) no . . N2 C1 2.963(6) no . . N2 C10 3.065(6) no . . C4 C7 2.767(7) no . . C4 C10 3.171(6) no . . C5 C8 2.822(8) no . . C6 C9 2.756(7) no . . C9 C10 3.153(7) no . . I1 O1 3.590(3) no . 2_545 I1 N1 3.579(4) no . 4_454 O1 I1 3.590(3) no . 2_555 O1 N1 2.892(6) no . 3_666 O1 N2 3.018(5) no . 2_656 O2 N1 2.842(5) no . 3_656 O2 N2 2.893(5) no . 2_646 O2 C3 3.556(7) no . 3_656 N1 I1 3.579(4) no . 4_655 N1 O1 2.892(6) no . 3_666 N1 O2 2.842(5) no . 3_656 N1 N1 3.531(5) no . 3_666 N1 N2 3.482(6) no . 4_554 N2 O1 3.018(5) no . 2_646 N2 O2 2.893(5) no . 2_656 N2 N1 3.482(6) no . 4_555 C3 O2 3.556(7) no . 3_656 C8 C8 3.564(7) no . 3_566 I1 H9 3.0744 no . . I1 H10 3.0656 no . . O1 H1 2.4459 no . . O1 H2 3.0283 no . . O1 H4 3.0043 no . . O1 H6 2.3309 no . . O2 H2 3.1522 no . . O2 H3 2.4302 no . . O2 H4 3.0163 no . . O2 H7 2.9719 no . . O2 H8 2.5812 no . . N1 H7 2.4840 no . . N2 H5 2.8712 no . . N2 H6 3.0564 no . . C1 H4 2.6681 no . . C1 H7 3.2712 no . . C1 H8 2.8513 no . . C1 H11 2.8572 no . . C2 H1 3.2630 no . . C2 H2 2.5392 no . . C2 H3 3.2647 no . . C2 H4 2.5431 no . . C3 H2 2.5868 no . . C3 H5 2.8563 no . . C3 H6 3.2696 no . . C3 H9 2.8371 no . . C4 H2 3.5711 no . . C4 H5 2.9164 no . . C4 H6 3.1493 no . . C4 H11 3.2750 no . . C5 H7 2.8182 no . . C5 H8 3.0153 no . . C5 H10 3.2916 no . . C6 H11 3.2619 no . . C7 H9 3.2986 no . . C8 H5 3.0429 no . . C8 H6 2.8532 no . . C9 H7 3.1453 no . . C9 H8 2.8954 no . . C9 H9 3.2881 no . . C9 H10 3.2554 no . . C10 H4 2.9943 no . . C10 H5 3.3514 no . . C10 H6 2.5537 no . . C10 H7 2.6379 no . . C10 H8 3.3999 no . . C11 H2 3.0525 no . . C11 H5 2.6771 no . . C11 H6 3.0438 no . . C11 H7 2.9631 no . . C11 H8 2.6174 no . . H1 H7 3.2774 no . . H2 H7 1.9446 no . . H2 H8 3.2885 no . . H4 H5 2.6332 no . . H4 H6 2.5020 no . . H5 H8 2.9445 no . . H5 H11 3.1621 no . . H6 H11 2.8179 no . . H7 H9 2.7804 no . . H8 H9 3.1489 no . . H10 H11 2.3424 no . . I1 H1 3.3399 no . 4_454 I1 H5 3.3611 no . 3_556 I1 H8 3.5648 no . 2_555 I1 H9 3.5457 no . 2_555 I1 H11 3.1965 no . 4_554 O1 H1 2.0132 no . 3_666 O1 H2 3.3965 no . 3_666 O1 H3 2.2000 no . 2_656 O1 H4 3.5208 no . 2_656 O1 H10 3.1140 no . 3_566 O1 H11 3.5864 no . 3_566 O2 H1 3.1107 no . 3_656 O2 H2 2.0628 no . 3_656 O2 H3 3.0039 no . 2_646 O2 H4 2.2358 no . 2_646 O2 H7 2.5780 no . 3_656 N1 H1 2.8835 no . 3_666 N1 H3 3.1260 no . 4_554 N1 H4 3.2288 no . 4_554 N1 H7 3.3969 no . 3_656 N1 H8 3.3067 no . 3_656 N2 H1 3.0787 no . 4_555 N2 H2 3.3835 no . 4_555 N2 H4 3.4955 no . 2_646 N2 H10 3.2281 no . 4_655 C3 H2 3.1548 no . 3_656 C5 H5 3.1615 no . 3_556 C6 H5 2.9024 no . 3_556 C6 H9 3.3061 no . 2_555 C7 H3 3.5617 no . 4_454 C7 H5 3.4308 no . 3_556 C7 H6 3.4473 no . 3_566 C7 H8 3.0495 no . 3_556 C7 H9 3.3652 no . 2_555 C8 H8 3.1329 no . 3_556 C8 H11 3.0212 no . 3_566 C9 H11 3.5162 no . 3_566 C10 H1 2.7706 no . 3_666 C10 H3 3.2721 no . 2_656 C11 H2 3.1253 no . 3_656 C11 H4 3.1514 no . 2_646 C11 H7 3.4048 no . 3_656 H1 I1 3.3399 no . 4_655 H1 O1 2.0132 no . 3_666 H1 O2 3.1107 no . 3_656 H1 N1 2.8835 no . 3_666 H1 N2 3.0787 no . 4_554 H1 C10 2.7706 no . 3_666 H1 H1 2.3892 no . 3_666 H1 H3 2.5597 no . 4_554 H1 H4 3.0504 no . 4_554 H1 H8 3.3458 no . 3_656 H2 O1 3.3965 no . 3_666 H2 O2 2.0628 no . 3_656 H2 N2 3.3835 no . 4_554 H2 C3 3.1548 no . 3_656 H2 C11 3.1253 no . 3_656 H2 H2 3.2182 no . 3_656 H2 H3 3.1468 no . 4_554 H2 H4 2.9620 no . 4_554 H2 H7 2.8039 no . 3_656 H2 H8 2.8050 no . 3_656 H3 O1 2.2000 no . 2_646 H3 O2 3.0039 no . 2_656 H3 N1 3.1260 no . 4_555 H3 C7 3.5617 no . 4_655 H3 C10 3.2721 no . 2_646 H3 H1 2.5597 no . 4_555 H3 H2 3.1468 no . 4_555 H3 H4 3.1350 no . 2_646 H3 H6 3.3307 no . 2_646 H3 H10 2.6333 no . 4_655 H4 O1 3.5208 no . 2_646 H4 O2 2.2358 no . 2_656 H4 N1 3.2288 no . 4_555 H4 N2 3.4955 no . 2_656 H4 C11 3.1514 no . 2_656 H4 H1 3.0504 no . 4_555 H4 H2 2.9620 no . 4_555 H4 H3 3.1350 no . 2_656 H5 I1 3.3611 no . 3_556 H5 C5 3.1615 no . 3_556 H5 C6 2.9024 no . 3_556 H5 C7 3.4308 no . 3_556 H5 H9 3.3765 no . 3_556 H6 C7 3.4473 no . 3_566 H6 H3 3.3307 no . 2_656 H6 H9 3.5376 no . 4_555 H6 H10 2.8850 no . 3_566 H6 H11 3.2909 no . 3_566 H7 O2 2.5780 no . 3_656 H7 N1 3.3969 no . 3_656 H7 C11 3.4048 no . 3_656 H7 H2 2.8039 no . 3_656 H7 H7 3.5959 no . 3_656 H8 I1 3.5648 no . 2_545 H8 N1 3.3067 no . 3_656 H8 C7 3.0495 no . 3_556 H8 C8 3.1329 no . 3_556 H8 H1 3.3458 no . 3_656 H8 H2 2.8050 no . 3_656 H8 H10 3.0299 no . 3_556 H8 H11 3.1544 no . 3_556 H9 I1 3.5457 no . 2_545 H9 C6 3.3061 no . 2_545 H9 C7 3.3652 no . 2_545 H9 H5 3.3765 no . 3_556 H9 H6 3.5376 no . 4_554 H9 H10 3.3404 no . 2_545 H10 O1 3.1140 no . 3_566 H10 N2 3.2281 no . 4_454 H10 H3 2.6333 no . 4_454 H10 H6 2.8850 no . 3_566 H10 H8 3.0299 no . 3_556 H10 H9 3.3404 no . 2_555 H11 I1 3.1965 no . 4_555 H11 O1 3.5864 no . 3_566 H11 C8 3.0212 no . 3_566 H11 C9 3.5162 no . 3_566 H11 H6 3.2909 no . 3_566 H11 H8 3.1544 no . 3_556 H11 H11 2.7130 no . 3_566 #============================================================================== loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_D _geom_hbond_site_symmetry_H _geom_hbond_site_symmetry_A _geom_hbond_distance_DA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_angle_DHA _geom_hbond_publ_flag N1 H1 O1 . . 3_666 2.892(6) 0.880 2.013 176.8 no N1 H2 O2 . . 3_656 2.842(5) 0.880 2.063 147.1 no N2 H3 O1 . . 2_646 3.018(5) 0.880 2.200 154.5 no N2 H4 O2 . . 2_656 2.893(5) 0.880 2.236 131.3 no #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #==============================================================================