#------------------------------------------------------------------------------ #$Date: 2014-12-22 15:48:19 +0200 (Mon, 22 Dec 2014) $ #$Revision: 128996 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/11/60/7116064.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7116064 loop_ _publ_author_name 'Wei Ji' 'Guofeng Liu' 'Mingxin Xu' 'Xiaoqiu Dou' 'Chuanliang Feng' _publ_section_title ; Rational design of coumarin-based supramolecular hydrogelators for cell imaging ; _journal_coden_Cambridge 182 _journal_name_full Chem.Commun. _journal_page_first 15545 _journal_paper_doi 10.1039/C4cc06376G _journal_volume 50 _journal_year 2014 _chemical_formula_moiety 'C15 H9 N O4' _chemical_formula_sum 'C15 H9 N O4' _chemical_formula_weight 267.23 _chemical_name_systematic ; ? ; _space_group_crystal_system orthorhombic _space_group_IT_number 33 _space_group_name_Hall 'P 2c -2n' _space_group_name_H-M_alt 'P n a 21' _symmetry_space_group_name_Hall 'P 2c -2n' _symmetry_space_group_name_H-M 'P n a 21' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary heavy _audit_creation_date 2014-03-23 _audit_creation_method ; Olex2 1.2 (compiled 2014.03.12 svn.r2899 for OlexSys, GUI svn.r4796) ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 11.595(4) _cell_length_b 3.8440(14) _cell_length_c 26.917(8) _cell_measurement_reflns_used 819 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 19.43 _cell_measurement_theta_min 3.51 _cell_volume 1199.7(7) _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2008)' _computing_structure_solution 'XS (Sheldrick, 2008)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.992 _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0703 _diffrn_reflns_av_unetI/netI 0.0702 _diffrn_reflns_laue_measured_fraction_full 0.997 _diffrn_reflns_laue_measured_fraction_max 0.992 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 7992 _diffrn_reflns_point_group_measured_fraction_full 0.798 _diffrn_reflns_point_group_measured_fraction_max 0.763 _diffrn_reflns_theta_full 26.000 _diffrn_reflns_theta_max 30.121 _diffrn_reflns_theta_min 3.027 _exptl_absorpt_coefficient_mu 0.109 _exptl_absorpt_correction_type none _exptl_crystal_density_diffrn 1.480 _exptl_crystal_F_000 552 _refine_diff_density_max 0.180 _refine_diff_density_min -0.212 _refine_diff_density_rms 0.045 _refine_ls_abs_structure_details ; Flack x determined using 420 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons and Flack (2004), Acta Cryst. A60, s61). ; _refine_ls_abs_structure_Flack -0.1(10) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.848 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 181 _refine_ls_number_reflns 2716 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 0.848 _refine_ls_R_factor_all 0.1180 _refine_ls_R_factor_gt 0.0460 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details ; w=1/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1143 _refine_ls_wR_factor_ref 0.1623 _reflns_Friedel_coverage 0.507 _reflns_friedel_fraction_full 0.591 _reflns_friedel_fraction_max 0.524 _reflns_number_gt 1438 _reflns_number_total 2716 _reflns_threshold_expression 'I > 2\s(I)' _[local]_cod_data_source_file c4cc06376g2.cif _[local]_cod_data_source_block global _cod_database_code 7116064 _shelxl_version_number 2013-2 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups 2.a Aromatic/amide H refined with riding coordinates: C6(H6), C8(H8), C3(H3), C12(H12), C9(H9), C2(H2), C15(H15), C13(H13), C14(H14) ; _olex2_computing_structure_refinement_long 'ShelXL (Sheldrick, 2008)' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' 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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn O3 O 0.4932(3) 0.7768(8) 0.23712(12) 0.0479(8) Uani 1 1 d . C5 C 0.4780(4) 0.8796(11) 0.10269(18) 0.0414(10) Uani 1 1 d . O2 O 0.4024(3) 0.7929(8) 0.06510(12) 0.0552(9) Uani 1 1 d . C7 C 0.5177(4) 0.8768(10) 0.18846(16) 0.0401(10) Uani 1 1 d . C6 C 0.4443(4) 0.7920(10) 0.15004(17) 0.0421(10) Uani 1 1 d . H6 H 0.3746 0.6796 0.1559 0.050 Uiso 1 1 calc R C4 C 0.5815(4) 1.0467(11) 0.09275(18) 0.0438(10) Uani 1 1 d . C8 C 0.6208(4) 1.0464(11) 0.1806(2) 0.0473(11) Uani 1 1 d . H8 H 0.6682 1.1045 0.2072 0.057 Uiso 1 1 calc R N8 N 0.4591(3) 0.5930(11) 0.33148(14) 0.0498(10) Uani 1 1 d . C3 C 0.6077(5) 1.1236(13) 0.0417(2) 0.0581(14) Uani 1 1 d . H3 H 0.6769 1.2318 0.0337 0.070 Uiso 1 1 calc R C12 C 0.2592(4) 0.7432(13) 0.32596(19) 0.0528(12) Uani 1 1 d . H12 H 0.1990 0.8371 0.3075 0.063 Uiso 1 1 calc R O4 O 0.3229(3) 1.0518(10) 0.23479(14) 0.0640(10) Uani 1 1 d . C9 C 0.6525(4) 1.1282(11) 0.1330(2) 0.0527(13) Uani 1 1 d . H9 H 0.7225 1.2397 0.1273 0.063 Uiso 1 1 calc R C10 C 0.3895(4) 0.8721(12) 0.25648(17) 0.0442(10) Uani 1 1 d . C11 C 0.3699(4) 0.7279(11) 0.30690(19) 0.0435(10) Uani 1 1 d . C1 C 0.4259(5) 0.8653(15) 0.0158(2) 0.0612(14) Uani 1 1 d . C2 C 0.5330(5) 1.0406(15) 0.0058(2) 0.0637(15) Uani 1 1 d . H2 H 0.5510 1.0984 -0.0268 0.076 Uiso 1 1 calc R C15 C 0.4380(5) 0.4729(14) 0.3771(2) 0.0568(13) Uani 1 1 d . H15 H 0.4993 0.3814 0.3952 0.068 Uiso 1 1 calc R O1 O 0.3551(5) 0.7718(15) -0.01412(17) 0.0909(15) Uani 1 1 d . C13 C 0.2408(5) 0.6151(15) 0.3731(2) 0.0625(14) Uani 1 1 d . H13 H 0.1675 0.6230 0.3871 0.075 Uiso 1 1 calc R C14 C 0.3307(5) 0.4766(13) 0.3991(2) 0.0585(13) Uani 1 1 d . H14 H 0.3198 0.3871 0.4309 0.070 Uiso 1 1 calc R loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O3 0.0393(18) 0.0598(18) 0.0445(18) 0.0018(15) -0.0023(15) 0.0073(14) C5 0.036(2) 0.041(2) 0.047(3) -0.0008(19) -0.004(2) 0.0038(17) O2 0.048(2) 0.074(2) 0.0437(18) 0.0010(17) -0.0052(16) -0.0038(16) C7 0.037(2) 0.038(2) 0.046(3) 0.0006(19) -0.002(2) 0.0043(17) C6 0.035(2) 0.044(2) 0.047(3) -0.0007(19) 0.000(2) -0.0042(17) C4 0.037(2) 0.038(2) 0.056(3) 0.0026(19) 0.005(2) 0.0026(18) C8 0.037(2) 0.046(2) 0.059(3) -0.002(2) -0.008(2) 0.0018(18) N8 0.047(2) 0.055(2) 0.047(2) 0.0001(18) -0.006(2) 0.0079(18) C3 0.051(3) 0.050(3) 0.073(4) 0.013(3) 0.019(3) 0.009(2) C12 0.048(3) 0.053(2) 0.057(3) -0.007(2) -0.002(2) 0.003(2) O4 0.059(2) 0.078(2) 0.054(2) 0.0053(19) -0.0057(18) 0.0331(19) C9 0.032(2) 0.043(2) 0.083(4) 0.005(2) 0.000(2) -0.0053(18) C10 0.041(2) 0.048(2) 0.044(2) -0.009(2) -0.006(2) 0.0072(19) C11 0.040(2) 0.044(2) 0.047(2) -0.009(2) -0.009(2) 0.0077(18) C1 0.069(4) 0.068(3) 0.046(3) 0.007(2) 0.000(3) 0.010(3) C2 0.069(4) 0.073(4) 0.049(3) 0.013(3) 0.012(3) 0.010(3) C15 0.058(3) 0.062(3) 0.050(3) 0.006(2) -0.007(2) 0.005(2) O1 0.091(4) 0.129(4) 0.052(2) 0.001(2) -0.023(2) -0.002(3) C13 0.051(3) 0.068(3) 0.069(4) -0.004(3) 0.011(3) -0.001(3) C14 0.064(3) 0.059(3) 0.053(3) 0.001(3) 0.004(3) -0.003(3) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C10 O3 C7 117.7(3) O2 C5 C4 121.3(4) C6 C5 O2 116.2(4) C6 C5 C4 122.5(4) C5 O2 C1 122.0(4) C6 C7 O3 120.9(4) C6 C7 C8 122.1(4) C8 C7 O3 116.9(4) C5 C6 C7 117.6(4) C5 C4 C3 117.5(4) C5 C4 C9 117.7(4) C9 C4 C3 124.7(4) C9 C8 C7 119.1(4) C11 N8 C15 116.7(4) C2 C3 C4 120.4(5) C13 C12 C11 118.1(5) C8 C9 C4 121.0(4) O3 C10 C11 112.6(4) O4 C10 O3 122.8(4) O4 C10 C11 124.5(4) N8 C11 C12 123.5(5) N8 C11 C10 118.8(4) C12 C11 C10 117.7(4) O2 C1 C2 116.3(5) O1 C1 O2 116.6(5) O1 C1 C2 127.2(5) C3 C2 C1 122.4(5) N8 C15 C14 123.8(5) C14 C13 C12 119.6(5) C13 C14 C15 118.3(5) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O3 C7 1.394(5) O3 C10 1.360(5) C5 O2 1.379(6) C5 C6 1.375(6) C5 C4 1.387(7) O2 C1 1.384(6) C7 C6 1.378(6) C7 C8 1.378(6) C4 C3 1.437(7) C4 C9 1.396(7) C8 C9 1.370(7) N8 C11 1.332(6) N8 C15 1.336(6) C3 C2 1.336(8) C12 C11 1.384(7) C12 C13 1.377(8) O4 C10 1.189(5) C10 C11 1.483(7) C1 C2 1.438(8) C1 O1 1.204(7) C15 C14 1.378(8) C13 C14 1.364(8) 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 O3 C7 C6 C5 -175.8(4) O3 C7 C8 C9 175.5(4) O3 C10 C11 N8 13.9(6) O3 C10 C11 C12 -166.4(4) C5 O2 C1 C2 -0.8(7) C5 O2 C1 O1 178.5(5) C5 C4 C3 C2 1.1(7) C5 C4 C9 C8 -0.2(6) O2 C5 C6 C7 -179.7(4) O2 C5 C4 C3 -0.5(6) O2 C5 C4 C9 179.4(4) O2 C1 C2 C3 1.4(8) C7 O3 C10 O4 -4.4(6) C7 O3 C10 C11 175.6(3) C7 C8 C9 C4 0.9(7) C6 C5 O2 C1 -179.8(4) C6 C5 C4 C3 179.7(4) C6 C5 C4 C9 -0.4(6) C6 C7 C8 C9 -1.2(7) C4 C5 O2 C1 0.4(6) C4 C5 C6 C7 0.1(6) C4 C3 C2 C1 -1.6(8) C8 C7 C6 C5 0.7(6) N8 C15 C14 C13 -0.9(8) C3 C4 C9 C8 179.8(4) C12 C13 C14 C15 0.5(8) O4 C10 C11 N8 -166.1(5) O4 C10 C11 C12 13.6(7) C9 C4 C3 C2 -178.8(5) C10 O3 C7 C6 -55.2(5) C10 O3 C7 C8 128.2(4) C11 N8 C15 C14 1.1(7) C11 C12 C13 C14 -0.5(8) C15 N8 C11 C12 -1.0(6) C15 N8 C11 C10 178.6(4) O1 C1 C2 C3 -177.8(6) C13 C12 C11 N8 0.7(7) C13 C12 C11 C10 -178.9(5)