#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/68/2206817.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_2206817 loop_ _publ_author_name 'Guo, Cheng' 'Gu, Xi-Feng' _publ_section_title ; Ethyl 2-amino-4-(2-methoxyphenyl)-4H-benzo[h]chromene-3-carboxylate ; _journal_coeditor_code WW6412 _journal_issue 9 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o3104 _journal_page_last o3105 _journal_paper_doi 10.1107/S1600536805025018 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C23 H21 N O4' _chemical_formula_moiety 'C23 H21 N O4' _chemical_formula_sum 'C23 H21 N O4' _chemical_formula_weight 375.41 _chemical_name_systematic ; Ethyl 2-amino-4-(2-methoxyphenyl)-4H-benzo[h]chromene-3-carboxylate ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 101.45(3) _cell_angle_beta 96.33(3) _cell_angle_gamma 96.82(3) _cell_formula_units_Z 2 _cell_length_a 6.9960(14) _cell_length_b 10.542(2) _cell_length_c 13.522(3) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 13 _cell_measurement_theta_min 10 _cell_volume 961.3(4) _computing_cell_refinement 'CAD-4 Software' _computing_data_collection 'CAD-4 Software (Enraf--Nonius, 1989)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_molecular_graphics 'SHELXTL (Siemens, 1996)' _computing_publication_material SHELXTL _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _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 0.0514 _diffrn_reflns_av_sigmaI/netI 0.0411 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 4100 _diffrn_reflns_theta_full 25.97 _diffrn_reflns_theta_max 25.97 _diffrn_reflns_theta_min 1.55 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time 120 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type none _exptl_crystal_colour Colourless _exptl_crystal_density_diffrn 1.297 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Block _exptl_crystal_F_000 396 _exptl_crystal_size_max .4 _exptl_crystal_size_mid .3 _exptl_crystal_size_min .2 _refine_diff_density_max 0.227 _refine_diff_density_min -0.219 _refine_ls_extinction_coef 0.050(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 262 _refine_ls_number_reflns 3775 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.048 _refine_ls_R_factor_all 0.0997 _refine_ls_R_factor_gt 0.0566 _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^)+(0.09P)^2^+0.2P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1574 _refine_ls_wR_factor_ref 0.1874 _reflns_number_gt 2310 _reflns_number_total 3775 _reflns_threshold_expression I>2\s(I) _cod_data_source_file ww6412.cif _cod_data_source_block I _cod_original_cell_volume 961.3(3) _cod_database_code 2206817 _cod_database_fobs_code 2206817 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -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_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_type_symbol O1 0.5852(2) 0.72409(16) 0.59936(13) 0.0624(5) Uani d . 1 O O2 0.2646(3) 0.67207(19) 0.54931(15) 0.0746(6) Uani d . 1 O O3 0.2670(2) 0.34957(15) 0.68622(13) 0.0562(5) Uani d . 1 O O4 0.4026(3) 0.5735(2) 0.87238(14) 0.0756(6) Uani d . 1 O N 0.0850(3) 0.4661(3) 0.60674(19) 0.0673(7) Uani d . 1 N C1 0.7846(5) 0.9007(3) 0.5603(3) 0.0999(11) Uani d . 1 C H1A 0.7868 0.9732 0.5272 0.150 Uiso calc R 1 H H1B 0.8667 0.8412 0.5306 0.150 Uiso calc R 1 H H1C 0.8308 0.9320 0.6316 0.150 Uiso calc R 1 H C2 0.5813(4) 0.8317(3) 0.5474(2) 0.0730(8) Uani d . 1 C H2A 0.4966 0.8911 0.5765 0.088 Uiso calc R 1 H H2B 0.5332 0.7990 0.4756 0.088 Uiso calc R 1 H C3 0.4136(4) 0.6500(2) 0.59612(17) 0.0543(6) Uani d . 1 C C4 0.4286(3) 0.5459(2) 0.65041(17) 0.0486(5) Uani d . 1 C C5 0.2668(3) 0.4590(2) 0.64685(17) 0.0508(6) Uani d . 1 C C6 0.4448(3) 0.3168(2) 0.72188(17) 0.0513(6) Uani d . 1 C C7 0.4318(4) 0.1904(2) 0.74412(17) 0.0549(6) Uani d . 1 C C8 0.2574(4) 0.1034(3) 0.7279(2) 0.0685(7) Uani d . 1 C H8A 0.1428 0.1275 0.7006 0.082 Uiso calc R 1 H C9 0.2555(5) -0.0168(3) 0.7520(3) 0.0871(9) Uani d . 1 C H9A 0.1398 -0.0744 0.7398 0.105 Uiso calc R 1 H C10 0.4245(6) -0.0536(3) 0.7945(3) 0.0923(11) Uani d . 1 C H10A 0.4204 -0.1345 0.8125 0.111 Uiso calc R 1 H C11 0.5953(5) 0.0275(3) 0.8101(2) 0.0836(9) Uani d . 1 C H11A 0.7075 0.0009 0.8379 0.100 Uiso calc R 1 H C12 0.6065(4) 0.1519(3) 0.78486(19) 0.0637(7) Uani d . 1 C C13 0.7822(4) 0.2386(3) 0.7979(2) 0.0699(8) Uani d . 1 C H13A 0.8973 0.2141 0.8243 0.084 Uiso calc R 1 H C14 0.7854(4) 0.3569(3) 0.77249(19) 0.0621(7) Uani d . 1 C H14A 0.9033 0.4115 0.7809 0.075 Uiso calc R 1 H C15 0.6138(3) 0.3993(2) 0.73355(17) 0.0506(6) Uani d . 1 C C16 0.6195(3) 0.5339(2) 0.70939(16) 0.0503(6) Uani d . 1 C H16A 0.7189 0.5418 0.6644 0.060 Uiso calc R 1 H C17 0.6856(3) 0.6386(2) 0.80602(17) 0.0545(6) Uani d . 1 C C18 0.8641(4) 0.7172(2) 0.8187(2) 0.0665(7) Uani d . 1 C H18A 0.9395 0.7075 0.7659 0.080 Uiso calc R 1 H C19 0.9331(5) 0.8090(3) 0.9067(3) 0.0835(9) Uani d . 1 C H19A 1.0537 0.8599 0.9131 0.100 Uiso calc R 1 H C20 0.8244(6) 0.8251(3) 0.9842(3) 0.0918(11) Uani d . 1 C H20A 0.8713 0.8873 1.0437 0.110 Uiso calc R 1 H C21 0.6441(6) 0.7499(3) 0.9759(2) 0.0811(9) Uani d . 1 C H21A 0.5697 0.7624 1.0290 0.097 Uiso calc R 1 H C22 0.5757(4) 0.6554(2) 0.88715(19) 0.0621(7) Uani d . 1 C C23 0.2869(5) 0.5797(4) 0.9540(2) 0.0950(11) Uani d . 1 C H23A 0.1709 0.5172 0.9326 0.143 Uiso calc R 1 H H23B 0.2525 0.6660 0.9719 0.143 Uiso calc R 1 H H23C 0.3598 0.5600 1.0121 0.143 Uiso calc R 1 H H2 0.080(4) 0.538(3) 0.579(2) 0.083(9) Uiso d . 1 H H1 0.005(4) 0.397(3) 0.594(2) 0.072(9) Uiso d . 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 0.0610(11) 0.0629(11) 0.0614(10) -0.0026(8) 0.0023(8) 0.0190(8) O2 0.0664(12) 0.0772(13) 0.0825(13) 0.0053(9) -0.0118(10) 0.0380(10) O3 0.0442(9) 0.0597(10) 0.0703(11) 0.0112(7) 0.0043(7) 0.0266(8) O4 0.0759(13) 0.0945(14) 0.0608(11) 0.0247(11) 0.0195(9) 0.0140(10) N 0.0454(13) 0.0769(17) 0.0865(17) 0.0066(12) 0.0000(11) 0.0403(14) C1 0.103(3) 0.092(2) 0.105(3) -0.019(2) 0.019(2) 0.038(2) C2 0.089(2) 0.0705(18) 0.0608(16) -0.0028(15) 0.0083(14) 0.0256(14) C3 0.0592(15) 0.0567(14) 0.0443(12) 0.0059(12) -0.0004(11) 0.0096(10) C4 0.0446(13) 0.0504(13) 0.0499(12) 0.0084(10) 0.0021(10) 0.0100(10) C5 0.0477(13) 0.0571(14) 0.0501(13) 0.0151(11) 0.0026(10) 0.0153(11) C6 0.0512(14) 0.0557(14) 0.0492(13) 0.0201(11) 0.0051(10) 0.0100(10) C7 0.0648(16) 0.0568(14) 0.0477(13) 0.0222(12) 0.0106(11) 0.0127(11) C8 0.0759(19) 0.0647(16) 0.0712(17) 0.0170(14) 0.0141(14) 0.0234(13) C9 0.113(3) 0.0661(18) 0.092(2) 0.0169(18) 0.0211(19) 0.0336(17) C10 0.136(3) 0.067(2) 0.092(2) 0.039(2) 0.028(2) 0.0363(17) C11 0.110(3) 0.083(2) 0.0753(19) 0.055(2) 0.0197(18) 0.0300(16) C12 0.0768(18) 0.0687(16) 0.0546(14) 0.0376(15) 0.0145(13) 0.0159(12) C13 0.0641(17) 0.089(2) 0.0660(16) 0.0450(16) 0.0098(13) 0.0194(14) C14 0.0499(14) 0.0775(18) 0.0606(15) 0.0231(13) 0.0030(11) 0.0130(13) C15 0.0484(13) 0.0556(14) 0.0467(12) 0.0158(11) 0.0036(10) 0.0053(10) C16 0.0426(12) 0.0586(14) 0.0483(12) 0.0090(10) 0.0046(10) 0.0080(10) C17 0.0585(15) 0.0544(14) 0.0512(13) 0.0164(12) -0.0004(11) 0.0126(11) C18 0.0665(17) 0.0564(15) 0.0719(17) 0.0055(13) -0.0104(13) 0.0152(13) C19 0.095(2) 0.0574(17) 0.087(2) 0.0016(16) -0.0219(19) 0.0131(15) C20 0.135(3) 0.0528(17) 0.074(2) 0.0123(19) -0.029(2) 0.0054(15) C21 0.124(3) 0.0723(19) 0.0518(16) 0.039(2) 0.0078(16) 0.0133(14) C22 0.0722(18) 0.0566(15) 0.0571(15) 0.0198(13) -0.0027(13) 0.0116(12) C23 0.092(2) 0.141(3) 0.0728(19) 0.056(2) 0.0362(17) 0.0361(19) 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 _geom_angle_publ_flag C3 O1 C2 116.1(2) yes C5 O3 C6 118.39(18) yes C22 O4 C23 118.9(2) yes C5 N H2 111.7(19) ? C5 N H1 117(2) ? H2 N H1 128(3) ? C2 C1 H1A 109.5 ? C2 C1 H1B 109.5 ? H1A C1 H1B 109.5 ? C2 C1 H1C 109.5 ? H1A C1 H1C 109.5 ? H1B C1 H1C 109.5 ? O1 C2 C1 107.4(2) yes O1 C2 H2A 110.2 ? C1 C2 H2A 110.2 ? O1 C2 H2B 110.2 ? C1 C2 H2B 110.2 ? H2A C2 H2B 108.5 ? O2 C3 O1 120.9(2) yes O2 C3 C4 126.2(2) yes O1 C3 C4 112.9(2) yes C5 C4 C3 118.3(2) yes C5 C4 C16 120.9(2) ? C3 C4 C16 120.8(2) yes C4 C5 N 126.9(2) yes C4 C5 O3 123.66(19) yes N C5 O3 109.4(2) yes C15 C6 O3 122.4(2) yes C15 C6 C7 123.8(2) ? O3 C6 C7 113.8(2) yes C8 C7 C6 123.5(2) yes C8 C7 C12 119.3(2) ? C6 C7 C12 117.2(2) ? C9 C8 C7 120.3(3) ? C9 C8 H8A 119.8 ? C7 C8 H8A 119.8 ? C8 C9 C10 120.6(3) ? C8 C9 H9A 119.7 ? C10 C9 H9A 119.7 ? C11 C10 C9 120.5(3) ? C11 C10 H10A 119.8 ? C9 C10 H10A 119.8 ? C10 C11 C12 121.3(3) ? C10 C11 H11A 119.4 ? C12 C11 H11A 119.4 ? C13 C12 C11 123.2(3) yes C13 C12 C7 118.9(2) ? C11 C12 C7 117.9(3) ? C14 C13 C12 121.0(2) ? C14 C13 H13A 119.5 ? C12 C13 H13A 119.5 ? C13 C14 C15 121.6(3) ? C13 C14 H14A 119.2 ? C15 C14 H14A 119.2 ? C6 C15 C14 117.5(2) ? C6 C15 C16 121.7(2) ? C14 C15 C16 120.7(2) yes C4 C16 C15 110.49(19) ? C4 C16 C17 115.16(18) yes C15 C16 C17 110.03(18) yes C4 C16 H16A 106.9 ? C15 C16 H16A 106.9 ? C17 C16 H16A 106.9 ? C18 C17 C22 117.5(2) ? C18 C17 C16 120.4(2) yes C22 C17 C16 122.1(2) yes C19 C18 C17 122.2(3) ? C19 C18 H18A 118.9 ? C17 C18 H18A 118.9 ? C20 C19 C18 119.7(3) ? C20 C19 H19A 120.1 ? C18 C19 H19A 120.1 ? C19 C20 C21 120.8(3) ? C19 C20 H20A 119.6 ? C21 C20 H20A 119.6 ? C20 C21 C22 119.3(3) ? C20 C21 H21A 120.3 ? C22 C21 H21A 120.3 ? O4 C22 C21 124.0(3) yes O4 C22 C17 115.6(2) yes C21 C22 C17 120.4(3) ? O4 C23 H23A 109.5 ? O4 C23 H23B 109.5 ? H23A C23 H23B 109.5 ? O4 C23 H23C 109.5 ? H23A C23 H23C 109.5 ? H23B C23 H23C 109.5 ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O1 C3 1.344(3) yes O1 C2 1.449(3) yes O2 C3 1.230(3) yes O3 C5 1.363(3) yes O3 C6 1.391(3) yes O4 C22 1.372(3) yes O4 C23 1.435(3) yes N C5 1.343(3) yes N H2 0.91(3) ? N H1 0.84(3) ? C1 C2 1.494(4) yes C1 H1A 0.9600 ? C1 H1B 0.9600 ? C1 H1C 0.9600 ? C2 H2A 0.9700 ? C2 H2B 0.9700 ? C3 C4 1.443(3) yes C4 C5 1.360(3) ? C4 C16 1.510(3) ? C6 C15 1.356(3) ? C6 C7 1.418(3) ? C7 C8 1.405(4) ? C7 C12 1.421(3) ? C8 C9 1.368(4) ? C8 H8A 0.9300 ? C9 C10 1.388(5) ? C9 H9A 0.9300 ? C10 C11 1.354(5) ? C10 H10A 0.9300 ? C11 C12 1.414(4) ? C11 H11A 0.9300 ? C12 C13 1.414(4) ? C13 C14 1.357(4) ? C13 H13A 0.9300 ? C14 C15 1.414(3) ? C14 H14A 0.9300 ? C15 C16 1.514(3) ? C16 C17 1.521(3) yes C16 H16A 0.9800 ? C17 C18 1.387(4) ? C17 C22 1.403(4) ? C18 C19 1.376(4) ? C18 H18A 0.9300 ? C19 C20 1.356(5) ? C19 H19A 0.9300 ? C20 C21 1.389(5) ? C20 H20A 0.9300 ? C21 C22 1.396(4) ? C21 H21A 0.9300 ? C23 H23A 0.9600 ? C23 H23B 0.9600 ? C23 H23C 0.9600 ? 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 N H2 O2 . 0.91(3) 1.93(3) 2.671(4) 137(2) yes C21 H21A Cg3 2_665 0.93 2.96 3.7227 141 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 C3 O1 C2 C1 179.9(2) C2 O1 C3 O2 1.6(3) C2 O1 C3 C4 -179.3(2) O2 C3 C4 C5 3.3(4) O1 C3 C4 C5 -175.7(2) O2 C3 C4 C16 -176.9(2) O1 C3 C4 C16 4.1(3) C3 C4 C5 N -7.7(4) C16 C4 C5 N 172.4(2) C3 C4 C5 O3 173.2(2) C16 C4 C5 O3 -6.7(3) C6 O3 C5 C4 -7.4(3) C6 O3 C5 N 173.3(2) C5 O3 C6 C15 10.5(3) C5 O3 C6 C7 -169.32(19) C15 C6 C7 C8 -177.3(2) O3 C6 C7 C8 2.5(3) C15 C6 C7 C12 2.7(3) O3 C6 C7 C12 -177.53(19) C6 C7 C8 C9 -179.4(2) C12 C7 C8 C9 0.6(4) C7 C8 C9 C10 1.2(5) C8 C9 C10 C11 -2.0(5) C9 C10 C11 C12 0.8(5) C10 C11 C12 C13 -178.7(3) C10 C11 C12 C7 1.1(4) C8 C7 C12 C13 178.0(2) C6 C7 C12 C13 -1.9(3) C8 C7 C12 C11 -1.8(3) C6 C7 C12 C11 178.3(2) C11 C12 C13 C14 180.0(2) C7 C12 C13 C14 0.2(4) C12 C13 C14 C15 1.0(4) O3 C6 C15 C14 178.7(2) C7 C6 C15 C14 -1.5(3) O3 C6 C15 C16 0.7(3) C7 C6 C15 C16 -179.5(2) C13 C14 C15 C6 -0.3(3) C13 C14 C15 C16 177.7(2) C5 C4 C16 C15 16.0(3) C3 C4 C16 C15 -163.9(2) C5 C4 C16 C17 -109.5(2) C3 C4 C16 C17 70.7(3) C6 C15 C16 C4 -13.1(3) C14 C15 C16 C4 169.0(2) C6 C15 C16 C17 115.2(2) C14 C15 C16 C17 -62.8(3) C4 C16 C17 C18 -122.2(2) C15 C16 C17 C18 112.1(2) C4 C16 C17 C22 61.0(3) C15 C16 C17 C22 -64.6(3) C22 C17 C18 C19 -0.2(4) C16 C17 C18 C19 -177.1(2) C17 C18 C19 C20 -0.4(4) C18 C19 C20 C21 0.1(5) C19 C20 C21 C22 0.9(4) C23 O4 C22 C21 -3.0(4) C23 O4 C22 C17 176.6(2) C20 C21 C22 O4 178.0(2) C20 C21 C22 C17 -1.5(4) C18 C17 C22 O4 -178.4(2) C16 C17 C22 O4 -1.6(3) C18 C17 C22 C21 1.2(3) C16 C17 C22 C21 178.0(2) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 2589660 2 PubChem 1211355