#------------------------------------------------------------------------------ #$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $ #$Revision: 176760 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/43/2014318.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2014318 loop_ _publ_author_name 'Jose G. Trujillo-Ferrara' 'Rosa Luisa Santill\'an-Baca' 'Norberto Farf\'an-Garc\'ia' 'Itzia I. Padilla-Mart\'inez' 'Efr\'en V. Garc\'ia-B\'aez' _publ_section_title ; Two isomeric butadiene--N-(acetoxyphenyl)maleimide Diels--Alder adducts: supramolecular structure directed by C---H···X (X = O and \p) hydrogen bonds and perpendicular dipole carbonyl--carbonyl interactions ; _journal_coeditor_code EM1003 _journal_issue 3 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o125 _journal_page_last o128 _journal_paper_doi 10.1107/S0108270106002186 _journal_volume 62 _journal_year 2006 _chemical_formula_iupac 'C16 H15 N O4' _chemical_formula_moiety 'C16 H15 N O4' _chemical_formula_sum 'C16 H15 N O4' _chemical_formula_weight 285.17 _chemical_name_systematic ; 4-(1,3-dioxo-2,3,3a,4,7,7a-hexahydro-1H-isoindol-2-yl)phenyl acetate ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90 _cell_angle_beta 93.73(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 16.1630(10) _cell_length_b 6.5780(10) _cell_length_c 13.5830(10) _cell_measurement_reflns_used 24 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 11 _cell_measurement_theta_min 10 _cell_volume 1441.1(3) _computing_cell_refinement 'CAD-4 Express' _computing_data_collection 'CAD-4 Express (Enraf--Nonius, 1995)' _computing_data_reduction 'JANA98 (Vaclav, 1998)' _computing_molecular_graphics 'WinGX (Farrugia, 1999)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 100(2) _diffrn_detector_area_resol_mean 3 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Enraf--Nonius CAD-4' _diffrn_measurement_method \w/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0200 _diffrn_reflns_av_sigmaI/netI 0.0347 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 3450 _diffrn_reflns_theta_full 27.96 _diffrn_reflns_theta_max 27.96 _diffrn_reflns_theta_min 2.53 _diffrn_standards_decay_% 2.5 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time 60 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type none _exptl_absorpt_process_details none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.314 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 600 _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.09 _refine_diff_density_max 0.426 _refine_diff_density_min -0.199 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.139 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 191 _refine_ls_number_reflns 3450 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.139 _refine_ls_R_factor_all 0.0897 _refine_ls_R_factor_gt 0.0505 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0946P)^2^+0.0607P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1663 _refine_ls_wR_factor_ref 0.1822 _reflns_number_gt 2056 _reflns_number_total 3450 _reflns_threshold_expression I>2\s(I) _cod_data_source_file em1003.cif _cod_data_source_block II _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2014318 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 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 0.1075(14) 0.0669(10) 0.0478(8) 0.0385(10) -0.0045(8) -0.0153(7) O3 0.0727(10) 0.0433(7) 0.0467(8) 0.0079(7) -0.0017(7) -0.0113(6) O14 0.0565(9) 0.0715(10) 0.0496(8) 0.0167(8) -0.0017(6) 0.0110(7) O15 0.0840(12) 0.0933(13) 0.0561(10) 0.0261(10) -0.0074(8) -0.0125(9) N2 0.0447(8) 0.0345(7) 0.0323(7) 0.0015(6) -0.0007(5) 0.0001(5) C1 0.0523(10) 0.0451(10) 0.0346(8) 0.0066(8) 0.0019(7) -0.0043(7) C3 0.0430(9) 0.0306(8) 0.0397(8) -0.0045(7) 0.0003(7) -0.0013(7) C3A 0.0439(10) 0.0374(9) 0.0430(9) -0.0027(8) 0.0003(7) 0.0064(7) C4 0.0587(13) 0.0656(14) 0.0536(12) 0.0191(11) -0.0019(9) 0.0069(10) C5 0.0415(11) 0.120(2) 0.0523(12) -0.0006(14) 0.0002(9) 0.0062(14) C6 0.0579(14) 0.097(2) 0.0564(13) -0.0329(14) -0.0130(10) 0.0133(13) C7 0.0812(16) 0.0655(14) 0.0490(11) 0.0009(12) -0.0214(10) -0.0095(10) C7A 0.0495(10) 0.0515(11) 0.0329(8) 0.0038(8) 0.0038(7) 0.0035(8) C8 0.0406(9) 0.0367(8) 0.0333(7) 0.0029(7) 0.0017(6) 0.0008(7) C9 0.0460(10) 0.0430(10) 0.0456(9) -0.0090(8) 0.0012(7) 0.0062(8) C10 0.0413(9) 0.0596(12) 0.0467(10) -0.0087(9) -0.0059(8) 0.0054(9) C11 0.0427(10) 0.0531(11) 0.0393(9) 0.0084(8) 0.0023(7) 0.0064(8) C12 0.0548(11) 0.0402(10) 0.0461(10) -0.0006(9) 0.0031(8) 0.0052(8) C13 0.0487(10) 0.0372(9) 0.0426(9) -0.0034(8) -0.0033(8) 0.0008(7) C15 0.0419(10) 0.0687(14) 0.0492(10) -0.0001(10) -0.0024(8) 0.0066(10) C16 0.0602(14) 0.0900(18) 0.0643(14) 0.0033(13) -0.0100(10) 0.0289(13) loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy O O1 0.24578(12) 1.0321(3) 0.36249(11) 0.0745(6) Uani . . 1.000 O O3 0.32688(9) 0.5160(2) 0.16956(10) 0.0545(5) Uani . . 1.000 O O14 0.09535(9) 1.1923(2) -0.05900(10) 0.0594(5) Uani . . 1.000 O O15 0.13805(12) 1.0021(3) -0.18105(12) 0.0783(7) Uani . . 1.000 N N2 0.27355(9) 0.7906(2) 0.24784(10) 0.0373(4) Uani . . 1.000 C C1 0.27588(12) 0.8706(3) 0.34267(12) 0.0440(5) Uani . . 1.000 C C3 0.31379(11) 0.6035(3) 0.24479(13) 0.0379(5) Uani . . 1.000 C C3A 0.33652(11) 0.5372(3) 0.34991(13) 0.0415(5) Uani . . 1.000 C C4 0.42418(13) 0.4502(4) 0.36141(17) 0.0595(8) Uani . . 1.000 C C5 0.48488(14) 0.6157(5) 0.35188(17) 0.0714(9) Uani . . 1.000 C C6 0.47444(15) 0.7922(5) 0.39272(17) 0.0712(9) Uani . . 1.000 C C7 0.40345(15) 0.8269(4) 0.45524(16) 0.0664(8) Uani . . 1.000 C C7A 0.32243(11) 0.7265(3) 0.41193(12) 0.0446(6) Uani . . 1.000 C C8 0.23068(10) 0.8862(3) 0.16447(12) 0.0369(5) Uani . . 1.000 C C9 0.16453(11) 0.7883(3) 0.11522(13) 0.0449(6) Uani . . 1.000 C C10 0.12072(12) 0.8847(3) 0.03805(14) 0.0496(6) Uani . . 1.000 C C11 0.14337(11) 1.0790(3) 0.01249(13) 0.0451(6) Uani . . 1.000 C C12 0.21008(12) 1.1761(3) 0.05959(14) 0.0470(6) Uani . . 1.000 C C13 0.25389(12) 1.0786(3) 0.13636(13) 0.0431(5) Uani . . 1.000 C C15 0.10087(12) 1.1449(4) -0.15435(15) 0.0535(7) Uani . . 1.000 C C16 0.05530(15) 1.2987(4) -0.21816(18) 0.0721(9) Uani . . 1.000 H H3A 0.29744 0.43167 0.36789 0.0499 Uiso . . 1.000 H H4B 0.43314 0.38597 0.42549 0.0715 Uiso . . 1.000 H H4C 0.43126 0.34819 0.31110 0.0715 Uiso . . 1.000 H H5 0.53125 0.59349 0.31620 0.0856 Uiso . . 1.000 H H6 0.51153 0.89718 0.38276 0.0852 Uiso . . 1.000 H H7A 0.28764 0.69095 0.46583 0.0535 Uiso . . 1.000 H H7B 0.39453 0.97201 0.46174 0.0796 Uiso . . 1.000 H H7C 0.41714 0.77245 0.52064 0.0796 Uiso . . 1.000 H H9 0.14962 0.65812 0.13401 0.0539 Uiso . . 1.000 H H10 0.07660 0.81969 0.00380 0.0595 Uiso . . 1.000 H H12 0.22543 1.30548 0.04003 0.0565 Uiso . . 1.000 H H13 0.29904 1.14239 0.16916 0.0518 Uiso . . 1.000 H H16A 0.05464 1.25628 -0.28583 0.1082 Uiso . . 1.000 H H16B 0.08257 1.42792 -0.21080 0.1082 Uiso . . 1.000 H H16C -0.00058 1.31050 -0.19883 0.1082 Uiso . . 1.000 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0030 0.0020 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C11 O14 C15 118.19(16) yes C1 N2 C3 112.17(14) yes C1 N2 C8 123.27(15) no C3 N2 C8 124.49(14) no O1 C1 N2 123.60(17) yes O1 C1 C7A 127.50(16) yes N2 C1 C7A 108.89(15) no O3 C3 N2 123.76(17) yes O3 C3 C3A 128.12(18) yes N2 C3 C3A 108.13(15) no C3 C3A C4 111.77(16) no C3 C3A C7A 104.43(15) no C4 C3A C7A 114.80(16) no C3A C4 C5 109.4(2) no C4 C5 C6 121.0(2) no C5 C6 C7 120.4(3) no C6 C7 C7A 112.46(19) no C1 C7A C3A 104.79(14) no C1 C7A C7 110.21(17) no C3A C7A C7 113.84(16) no N2 C8 C9 119.77(17) no N2 C8 C13 119.63(15) no C9 C8 C13 120.56(17) no C8 C9 C10 119.71(18) no C9 C10 C11 119.02(18) no O14 C11 C10 121.18(16) yes O14 C11 C12 116.95(17) yes C10 C11 C12 121.74(18) no C11 C12 C13 118.95(18) no C8 C13 C12 119.98(17) no O14 C15 O15 123.2(2) yes O14 C15 C16 110.0(2) no O15 C15 C16 126.9(2) no C3 C3A H3A 109 no C4 C3A H3A 109 no C7A C3A H3A 109 no C3A C4 H4B 110 no C3A C4 H4C 110 no C5 C4 H4B 110 no C5 C4 H4C 110 no H4B C4 H4C 108 no C4 C5 H5 119 no C6 C5 H5 120 no C5 C6 H6 120 no C7 C6 H6 120 no C6 C7 H7B 109 no C6 C7 H7C 109 no C7A C7 H7B 109 no C7A C7 H7C 109 no H7B C7 H7C 108 no C1 C7A H7A 109 no C3A C7A H7A 109 no C7 C7A H7A 109 no C8 C9 H9 120 no C10 C9 H9 120 no C9 C10 H10 120 no C11 C10 H10 120 no C11 C12 H12 121 no C13 C12 H12 121 no C8 C13 H13 120 no C12 C13 H13 120 no C15 C16 H16A 109 no C15 C16 H16B 109 no C15 C16 H16C 109 no H16A C16 H16B 109 no H16A C16 H16C 109 no H16B C16 H16C 109 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C1 . . 1.206(3) no O3 C3 . . 1.204(2) no O14 C11 . . 1.415(2) yes O14 C15 . . 1.341(2) yes O15 C15 . . 1.185(3) no N2 C1 . . 1.390(2) yes N2 C3 . . 1.394(2) yes N2 C8 . . 1.434(2) yes C1 C7A . . 1.503(3) no C3 C3A . . 1.515(3) no C3A C4 . . 1.527(3) no C3A C7A . . 1.529(3) no C4 C5 . . 1.477(4) no C5 C6 . . 1.302(4) no C6 C7 . . 1.489(3) no C7 C7A . . 1.548(3) no C8 C9 . . 1.383(3) no C8 C13 . . 1.381(3) no C9 C10 . . 1.381(3) no C10 C11 . . 1.380(3) no C11 C12 . . 1.375(3) no C12 C13 . . 1.380(3) no C15 C16 . . 1.495(3) no C3A H3A . . 0.98 no C4 H4B . . 0.97 no C4 H4C . . 0.97 no C5 H5 . . 0.93 no C6 H6 . . 0.93 no C7 H7B . . 0.97 no C7 H7C . . 0.97 no C7A H7A . . 0.98 no C9 H9 . . 0.93 no C10 H10 . . 0.93 no C12 H12 . . 0.93 no C13 H13 . . 0.93 no C16 H16A . . 0.96 no C16 H16B . . 0.96 no C16 H16C . . 0.96 no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_2 _geom_contact_publ_flag O1 C13 3.098(2) . no O1 C12 3.374(3) 4_575 no O1 C15 3.160(3) 4_575 no O1 C16 3.388(3) 4_575 no O3 C7 3.398(3) 4_564 no O3 C9 3.223(2) . no O3 C12 3.229(2) 1_545 no O3 C13 3.131(2) 1_545 no O15 C9 3.412(3) 4_564 no O15 C10 3.105(3) . no O15 N2 3.116(2) 4_564 no O15 C3A 3.219(3) 4_564 no O15 C1 3.314(3) 4_564 no O15 C3 3.152(3) 4_564 no O1 H16B 2.77 4_575 no O1 H12 2.68 4_575 no O1 H3A 2.76 1_565 no O1 H7B 2.71 . no O1 H13 2.91 . no O3 H4C 2.71 . no O3 H12 2.71 1_545 no O3 H13 2.50 1_545 no O3 H6 2.86 2_645 no O15 H3A 2.65 4_564 no O15 H9 2.74 4_564 no N2 O15 3.116(2) 4_565 no C1 O15 3.314(3) 4_565 no C3 C6 3.412(3) . no C3 O15 3.152(3) 4_565 no C3A O15 3.219(3) 4_565 no C6 C3 3.412(3) . no C7 O3 3.398(3) 4_565 no C9 O15 3.412(3) 4_565 no C9 O3 3.223(2) . no C10 O15 3.105(3) . no C12 O1 3.374(3) 4_574 no C12 O3 3.229(2) 1_565 no C13 O3 3.131(2) 1_565 no C13 O1 3.098(2) . no C15 O1 3.160(3) 4_574 no C16 O1 3.388(3) 4_574 no C1 H13 3.00 . no C3 H9 2.99 . no C4 H7C 3.04 . no C5 H4C 3.08 2_655 no C6 H4B 3.04 3_666 no C7 H4B 2.97 . no C8 H7A 2.95 4_564 no C9 H16C 3.02 3_575 no C9 H7A 2.94 4_564 no C10 H7A 2.97 4_564 no C11 H7A 3.03 4_564 no C12 H7A 3.04 4_564 no C13 H7A 3.00 4_564 no C15 H10 3.07 . no H3A O1 2.76 1_545 no H3A O15 2.65 4_565 no H4B C7 2.97 . no H4B C6 3.04 3_666 no H4C O3 2.71 . no H4C C5 3.08 2_645 no H4C H5 2.51 2_645 no H5 H4C 2.51 2_655 no H6 O3 2.86 2_655 no H7A C8 2.95 4_565 no H7A C9 2.94 4_565 no H7A C10 2.97 4_565 no H7A C11 3.03 4_565 no H7A C12 3.04 4_565 no H7A C13 3.00 4_565 no H7B O1 2.71 . no H7C C4 3.04 . no H9 C3 2.99 . no H9 O15 2.74 4_565 no H10 C15 3.07 . no H12 O3 2.71 1_565 no H12 O1 2.68 4_574 no H13 O1 2.91 . no H13 O3 2.50 1_565 no H13 C1 3.00 . no H16B O1 2.77 4_574 no H16C C9 3.02 3_575 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag C13 H13 O3 1_565 0.93 2.50 3.131(2) 125 yes C7A H7A Cg3 4_565 0.98 2.65 3.611(2) 167 yes 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 C15 O14 C11 C10 -76.1(2) no C15 O14 C11 C12 108.1(2) no C11 O14 C15 O15 6.9(3) no C11 O14 C15 C16 -172.12(17) no C3 N2 C1 O1 179.2(2) no C3 N2 C1 C7A 0.3(2) no C8 N2 C1 O1 -3.9(3) no C8 N2 C1 C7A 177.27(15) no C1 N2 C3 O3 -172.18(18) no C1 N2 C3 C3A 7.7(2) no C8 N2 C3 O3 10.9(3) no C8 N2 C3 C3A -169.19(15) no C1 N2 C8 C9 -116.7(2) no C1 N2 C8 C13 60.9(2) no C3 N2 C8 C9 59.9(2) no C3 N2 C8 C13 -122.54(19) no O1 C1 C7A C3A 173.2(2) no O1 C1 C7A C7 -63.9(3) no N2 C1 C7A C3A -8.0(2) no N2 C1 C7A C7 114.85(17) no O3 C3 C3A C4 43.0(3) no O3 C3 C3A C7A 167.67(19) no N2 C3 C3A C4 -136.89(17) no N2 C3 C3A C7A -12.20(19) no C3 C3A C4 C5 70.2(2) no C7A C3A C4 C5 -48.5(2) no C3 C3A C7A C1 11.94(18) no C3 C3A C7A C7 -108.55(17) no C4 C3A C7A C1 134.67(17) no C4 C3A C7A C7 14.2(2) no C3A C4 C5 C6 41.4(3) no C4 C5 C6 C7 3.8(4) no C5 C6 C7 C7A -40.6(3) no C6 C7 C7A C1 -88.7(2) no C6 C7 C7A C3A 28.7(3) no N2 C8 C9 C10 176.80(16) no C13 C8 C9 C10 -0.8(3) no N2 C8 C13 C12 -176.48(16) no C9 C8 C13 C12 1.1(3) no C8 C9 C10 C11 -0.9(3) no C9 C10 C11 O14 -173.36(17) no C9 C10 C11 C12 2.3(3) no O14 C11 C12 C13 173.84(17) no C10 C11 C12 C13 -2.0(3) no C11 C12 C13 C8 0.3(3) no