#------------------------------------------------------------------------------ #$Date: 2025-08-19 20:30:04 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301811 $ #$URL: svn://www.crystallography.net/cod/cif/4/00/00/4000036.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_4000036 loop_ _publ_author_name 'Muthuraman, Meiyappan' 'Masse, Ren\'e' 'Nicoud, Jean-Fran\,cois' 'Desiraju, Gautam R.' _publ_section_title ; Molecular Complexation as a Design Tool in the Crystal Engineering of Noncentrosymmetric Structures. Ideal Orientation of Chromophores Linked by O--H···O and C--H···O Hydrogen Bonds for Nonlinear Optics ; _journal_coden_ASTM CMATEX _journal_issue 5 _journal_name_full 'Chemistry of Materials' _journal_page_first 1473 _journal_page_last 1479 _journal_paper_doi 10.1021/cm000927y _journal_volume 13 _journal_year 2001 _chemical_formula_sum 'C18 H16 N2 O4' _chemical_formula_weight 324.34 _space_group_IT_number 4 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 1 21 1' _cell_angle_alpha 90 _cell_angle_beta 94.719(10) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 5.6171(5) _cell_length_b 7.75550(10) _cell_length_c 18.185(2) _cell_measurement_reflns_used 3100 _cell_measurement_temperature 296.2 _cell_measurement_theta_max 20.92 _cell_measurement_theta_min 2.08 _cell_volume 789.52(9) _diffrn_ambient_temperature 296.2 _diffrn_measurement_device Nonius-KappaCCD _diffrn_measurement_method 'Data from \f = 1\%, \f scans' _diffrn_orient_matrix_UB_11 0.00000 _diffrn_orient_matrix_UB_12 0.00000 _diffrn_orient_matrix_UB_13 0.00000 _diffrn_orient_matrix_UB_21 0.00000 _diffrn_orient_matrix_UB_22 0.00000 _diffrn_orient_matrix_UB_23 0.00000 _diffrn_orient_matrix_UB_31 0.00000 _diffrn_orient_matrix_UB_32 0.00000 _diffrn_orient_matrix_UB_33 0.00000 _diffrn_radiation_detector CCD _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type 'Ag K\a' _diffrn_radiation_wavelength 0.5608 _diffrn_reflns_av_R_equivalents 0.02519 _diffrn_reflns_av_sigmaI/netI 0.108 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 6200 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_reflns_theta_max 20.92 _diffrn_reflns_theta_min 2.08 _diffrn_standards_decay_% 0.00 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.364 _exptl_crystal_density_meas ? _exptl_crystal_description NONE _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.35 _reflns_number_gt 1387 _reflns_number_total 1720 _reflns_threshold_expression I>2.00\s(I) _cod_original_sg_symbol_H-M 'P 21' _cod_original_formula_sum 'C18 H16 N2 O4 ' _cod_database_code 4000036 loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' ' -x,1/2+y, -z' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_refinement_flags _atom_site_adp_type _atom_site_calc_flag _atom_site_calc_attached_atom O(1) 0.0821(2) 0.0000 1.19277(7) 0.0524(4) 1.000 . Uani d ? O(2) 0.3378(4) -0.0393(3) 0.62442(9) 0.0773(6) 1.000 . Uani d ? O(3) 0.6586(4) 0.1023(4) 0.65588(9) 0.0872(7) 1.000 . Uani d ? O(4) 0.3436(3) 0.1762(3) 1.28728(8) 0.0635(5) 1.000 . Uani d ? N(1) 0.4762(4) 0.0308(3) 0.67129(11) 0.0597(7) 1.000 . Uani d ? N(2) 0.4959(3) 0.0817(3) 1.33057(10) 0.0495(5) 1.000 . Uani d ? C(1) 0.1465(3) 0.0066(3) 1.12164(10) 0.0374(5) 1.000 . Uani d ? C(2) 0.0001(4) -0.0765(3) 1.06764(12) 0.0446(6) 1.000 . Uani d ? C(3) 0.0565(3) -0.0757(3) 0.99538(12) 0.0425(6) 1.000 . Uani d ? C(4) 0.2586(3) 0.0107(3) 0.97331(9) 0.0315(5) 1.000 . Uani d ? C(5) 0.4026(3) 0.0937(3) 1.02899(10) 0.0387(5) 1.000 . Uani d ? C(6) 0.3476(3) 0.0922(3) 1.10230(11) 0.0408(6) 1.000 . Uani d ? C(7) 0.3134(3) 0.0151(3) 0.89542(10) 0.0348(5) 1.000 . Uani d ? C(8) 0.1669(4) -0.0638(4) 0.83965(11) 0.0480(6) 1.000 . Uani d ? C(9) 0.2160(4) -0.0595(4) 0.76600(12) 0.0549(7) 1.000 . Uani d ? C(10) 0.4171(4) 0.0259(3) 0.74792(11) 0.0446(6) 1.000 . Uani d ? C(11) 0.5674(4) 0.1082(4) 0.80083(12) 0.0502(6) 1.000 . Uani d ? C(12) 0.5162(4) 0.1012(4) 0.87375(11) 0.0469(6) 1.000 . Uani d ? C(13) 0.6801(4) 0.0013(4) 1.30316(11) 0.0530(7) 1.000 . Uani d ? C(14) 0.8362(4) -0.0924(4) 1.34868(12) 0.0552(7) 1.000 . Uani d ? C(15) 0.8090(4) -0.1083(4) 1.42319(12) 0.0496(7) 1.000 . Uani d ? C(16) 0.6199(4) -0.0235(4) 1.44934(11) 0.0558(7) 1.000 . Uani d ? C(17) 0.4638(4) 0.0715(4) 1.40367(12) 0.0551(7) 1.000 . Uani d ? C(18) 0.9797(5) -0.2143(4) 1.47317(13) 0.0717(9) 1.000 . Uani d ? H(1) 0.2208 0.0779 1.2274 0.031 1.000 . Uiso c ? H(2) -0.1574 -0.1417 1.0823 0.076 1.000 . Uiso c ? H(3) -0.0572 -0.1434 0.9548 0.076 1.000 . Uiso c ? H(4) 0.5602 0.1596 1.0149 0.076 1.000 . Uiso c ? H(5) 0.4610 0.1585 1.1434 0.076 1.000 . Uiso c ? H(6) 0.0094 -0.1308 0.8541 0.076 1.000 . Uiso c ? H(7) 0.0996 -0.1212 0.7242 0.076 1.000 . Uiso c ? H(8) 0.7221 0.1766 0.7852 0.076 1.000 . Uiso c ? H(9) 0.6338 0.1640 0.9150 0.076 1.000 . Uiso c ? H(10) 0.7040 0.0090 1.2452 0.076 1.000 . Uiso c ? H(11) 0.9856 -0.1545 1.3262 0.076 1.000 . Uiso c ? H(12) 0.5920 -0.0323 1.5072 0.076 1.000 . Uiso c ? H(13) 0.3169 0.1370 1.4257 0.076 1.000 . Uiso c ? H(14) 0.9422 -0.1945 1.5293 0.076 1.000 . Uiso c ? H(15) 0.9555 -0.3491 1.4586 0.076 1.000 . Uiso c ? H(16) 1.1602 -0.1762 1.4652 0.076 1.000 . Uiso c ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 139089080