#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/02/2200212.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_2200212 loop_ _publ_author_name 'H\"okelek, Tuncer' 'Kaya, Elif Ece' 'K\?il\?i\,c, Zeynel' _publ_section_title 2,7-Dioxa-15,19-diazatricyclo[19,4,0,0^8,13^]pentacosa-8,10,12,21,23,25(1)-hexaene _journal_issue 4 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o309 _journal_page_last o311 _journal_paper_doi 10.1107/S1600536801003889 _journal_volume 57 _journal_year 2001 _chemical_formula_iupac 'C21 H24 N2 O2' _chemical_formula_moiety 'C21 H24 N2 O2' _chemical_formula_sum 'C21 H24 N2 O2' _chemical_formula_weight 336.43 _space_group_IT_number 15 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 1' _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 103.044(8) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 14.231(8) _cell_length_b 15.6630(14) _cell_length_c 8.206(4) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 18 _cell_measurement_theta_min 10 _cell_volume 1781.9(13) _computing_cell_refinement 'CAD-4 Software' _computing_data_collection 'CAD-4 Software (Enraf-Nonius, 1989)' _computing_data_reduction 'CAD-4 Software' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full .998 _diffrn_measured_fraction_theta_max .998 _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 .71073 _diffrn_reflns_av_R_equivalents .0337 _diffrn_reflns_av_sigmaI/netI .0304 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 3554 _diffrn_reflns_theta_full 26.31 _diffrn_reflns_theta_max 26.31 _diffrn_reflns_theta_min 2.60 _diffrn_standards_decay_% 1 _diffrn_standards_interval_time 120 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .081 _exptl_absorpt_correction_T_max .984 _exptl_absorpt_correction_T_min .975 _exptl_absorpt_correction_type '\y scans' _exptl_absorpt_process_details '(MolEN; Fair, 1990)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.255 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block-like _exptl_crystal_F_000 724 _exptl_crystal_size_max .30 _exptl_crystal_size_mid .25 _exptl_crystal_size_min .20 _refine_diff_density_max .143 _refine_diff_density_min -.151 _refine_ls_extinction_coef .063(3) _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_hydrogen_treatment refU _refine_ls_matrix_type full _refine_ls_number_parameters 127 _refine_ls_number_reflns 1816 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.057 _refine_ls_R_factor_all .0461 _refine_ls_R_factor_gt .0362 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean <0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0488P)^2^+0.3494P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .1060 _reflns_number_gt 1468 _reflns_number_total 1816 _reflns_threshold_expression I>2\s(I) _cod_data_source_file ob6032.cif _cod_data_source_block I _cod_original_sg_symbol_H-M 'C 2/c' _cod_database_code 2200212 _cod_database_fobs_code 2200212 loop_ _symmetry_equiv_pos_as_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' '-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_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol O1 .13740(5) .49049(5) .25488(12) .0515(3) Uani d . 1 . . O N1 .14349(6) .23658(6) .30725(12) .0448(3) Uani d . 1 . . N C9 .21554(7) .45222(7) .21602(14) .0417(3) Uani d . 1 . . C C4 .21878(7) .36282(7) .23047(13) .0392(3) Uani d . 1 . . C C3 .14552(7) .31686(7) .29760(13) .0396(3) Uani d . 1 . . C H31 .0989 .3483 .3344 .054(4) Uiso calc R 1 . . H C7 .36222(9) .45047(8) .11910(17) .0551(3) Uani d . 1 . . C H71 .4107 .4797 .0830 .069(4) Uiso calc R 1 . . H C10 .13676(8) .58169(7) .27145(15) .0448(3) Uani d . 1 . . C H101 .1388 .6089 .1661 .053(4) Uiso calc R 1 . . H H102 .1920 .6006 .3559 .048(3) Uiso calc R 1 . . H C5 .29414(8) .31938(8) .18443(15) .0458(3) Uani d . 1 . . C H51 .2966 .2601 .1916 .054(4) Uiso calc R 1 . . H C2 .06875(8) .19826(7) .37952(14) .0441(3) Uani d . 1 . . C H21 .0331 .2429 .4210 .048(3) Uiso calc R 1 . . H H22 .0985 .1622 .4732 .049(3) Uiso calc R 1 . . H C6 .36528(9) .36251(8) .12842(16) .0540(3) Uani d . 1 . . C H61 .4149 .3326 .0972 .070(4) Uiso calc R 1 . . H C11 .04434(8) .60372(7) .32230(15) .0461(3) Uani d . 1 . . C H111 .0510 .6598 .3738 .056(4) Uiso calc R 1 . . H H112 .0343 .5630 .4058 .055(4) Uiso calc R 1 . . H C1 .0000 .14535(9) .2500 .0410(4) Uani d S 1 . . C H11 -.0374 .1088 .3069 .045(3) Uiso d R 1 . . H C8 .28829(8) .49578(8) .16253(16) .0509(3) Uani d . 1 . . C H81 .2872 .5551 .1561 .055(4) Uiso calc R 1 . . H 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 .0404(5) .0348(4) .0850(6) -.0048(3) .0262(4) -.0088(4) N1 .0400(5) .0412(5) .0545(6) -.0019(4) .0135(4) -.0035(4) C9 .0349(5) .0429(6) .0481(6) -.0053(4) .0109(4) -.0107(4) C4 .0339(5) .0423(6) .0405(5) -.0039(4) .0066(4) -.0076(4) C3 .0357(5) .0418(6) .0410(6) -.0008(4) .0080(4) -.0072(4) C7 .0430(6) .0617(8) .0663(8) -.0136(6) .0242(6) -.0126(6) C10 .0433(6) .0344(6) .0572(7) -.0046(5) .0127(5) -.0034(5) C5 .0424(6) .0448(6) .0510(7) .0015(5) .0119(5) -.0069(5) C2 .0457(6) .0434(6) .0448(6) .0000(5) .0139(5) .0021(5) C6 .0417(6) .0614(8) .0630(7) .0008(5) .0207(5) -.0139(6) C11 .0474(7) .0390(6) .0529(7) -.0001(5) .0135(5) -.0068(5) C1 .0439(8) .0316(7) .0511(9) .000 .0180(7) .000 C8 .0450(7) .0456(7) .0650(8) -.0124(5) .0184(6) -.0109(5) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0106 .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_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C9 O1 C10 . . 118.88(8) yes C3 N1 C2 . . 117.71(10) yes O1 C9 C8 . . 124.24(11) yes O1 C9 C4 . . 115.57(9) yes C8 C9 C4 . . 120.18(10) no C5 C4 C9 . . 118.47(10) no C5 C4 C3 . . 121.09(10) yes C9 C4 C3 . . 120.41(9) yes N1 C3 C4 . . 122.64(10) yes N1 C3 H31 . . 118.7 no C4 C3 H31 . . 118.7 no C6 C7 C8 . . 121.01(11) no C6 C7 H71 . . 119.5 no C8 C7 H71 . . 119.5 no O1 C10 C11 . . 106.19(9) yes O1 C10 H101 . . 110.5 no C11 C10 H101 . . 110.5 no O1 C10 H102 . . 110.5 no C11 C10 H102 . . 110.5 no H101 C10 H102 . . 108.7 no C6 C5 C4 . . 121.28(11) no C6 C5 H51 . . 119.4 no C4 C5 H51 . . 119.4 no N1 C2 C1 . . 110.72(9) yes N1 C2 H21 . . 109.5 no C1 C2 H21 . . 109.5 no N1 C2 H22 . . 109.5 no C1 C2 H22 . . 109.5 no H21 C2 H22 . . 108.1 no C5 C6 C7 . . 119.42(11) no C5 C6 H61 . . 120.3 no C7 C6 H61 . . 120.3 no C10 C11 C11 . 2 113.92(12) yes C10 C11 H111 . . 108.8 no C11 C11 H111 2 . 108.8 no C10 C11 H112 . . 108.8 no C11 C11 H112 2 . 108.8 no H111 C11 H112 . . 107.7 no C2 C1 C2 . 2 113.81(13) yes C2 C1 H11 . . 108.8 no C2 C1 H11 2 . 108.8 no C7 C8 C9 . . 119.61(12) no C7 C8 H81 . . 120.2 no C9 C8 H81 . . 120.2 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C9 . 1.3629(14) yes O1 C10 . 1.4350(13) yes N1 C3 . 1.2607(14) yes N1 C2 . 1.4587(15) yes C9 C8 . 1.3912(16) no C9 C4 . 1.4052(16) yes C4 C5 . 1.3924(16) no C4 C3 . 1.4724(16) yes C3 H31 . .9300 no C7 C6 . 1.3799(19) no C7 C8 . 1.3808(17) no C7 H71 . .9300 no C10 C11 . 1.5069(18) yes C10 H101 . .9700 no C10 H102 . .9700 no C5 C6 . 1.3793(17) no C5 H51 . .9300 no C2 C1 . 1.5181(14) yes C2 H21 . .9700 no C2 H22 . .9700 no C6 H61 . .9300 no C11 C11 2 1.525(2) yes C11 H111 . .9700 no C11 H112 . .9700 no C1 C2 2 1.5181(14) no C1 H11 . .9700 no C8 H81 . .9300 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_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C10 O1 C9 C8 . . -11.67(16) no C10 O1 C9 C4 . . 169.33(10) no O1 C9 C4 C5 . . 176.77(10) no C8 C9 C4 C5 . . -2.28(15) no O1 C9 C4 C3 . . -5.03(14) no C8 C9 C4 C3 . . 175.92(10) no C2 N1 C3 C4 . . 178.64(9) yes C5 C4 C3 N1 . . -4.47(16) no C9 C4 C3 N1 . . 177.37(10) no C9 O1 C10 C11 . . -177.35(9) yes C9 C4 C5 C6 . . 1.07(16) no C3 C4 C5 C6 . . -177.12(10) no C3 N1 C2 C1 . . 115.50(11) yes C4 C5 C6 C7 . . .55(18) no C8 C7 C6 C5 . . -1.0(2) no O1 C10 C11 C11 . 2 -79.17(9) yes N1 C2 C1 C2 . 2 -73.83(8) yes C6 C7 C8 C9 . . -.21(19) no O1 C9 C8 C7 . . -177.09(11) no C4 C9 C8 C7 . . 1.87(17) no C10 C11 C11 C10 2 2 151.00(10) yes loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 11024175