#------------------------------------------------------------------------------ #$Date: 2019-10-05 03:37:53 +0300 (Sat, 05 Oct 2019) $ #$Revision: 219101 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/23/43/7234393.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_7234393 loop_ _publ_author_name 'Shishkina, Svitlana V.' 'Konovalova, Irina S.' 'Kovalenko, Sergiy Mykolayovich' 'Trostianko , Pavlo V.' 'Geleverya, Anna O.' 'Bunyatyan, Natalya D.' _publ_section_title ; Hydrogen bonding vs stacking interaction in the crystals of the simplest coumarin derivatives: study from the energetic viewpoint ; _journal_name_full CrystEngComm _journal_paper_doi 10.1039/C9CE01344J _journal_year 2019 _chemical_formula_sum 'C10 H7 N O3' _chemical_formula_weight 189.17 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2016/6 _audit_update_record ; 2019-08-23 deposited with the CCDC. 2019-10-04 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 95.601(5) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 4.7630(2) _cell_length_b 14.3440(9) _cell_length_c 12.3505(7) _cell_measurement_reflns_used 1174 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 30.074 _cell_measurement_theta_min 4.368 _cell_volume 839.76(8) _computing_structure_refinement 'SHELXL-2016/6 (Sheldrick, 2016)' _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 16.1827 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Xcalibur, Sapphire3' _diffrn_measurement_method '\w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0446 _diffrn_reflns_av_unetI/netI 0.0363 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 5565 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 24.992 _diffrn_reflns_theta_max 24.992 _diffrn_reflns_theta_min 3.289 _diffrn_source 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.113 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.82161 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour light-yellow _exptl_crystal_density_diffrn 1.496 _exptl_crystal_description stick _exptl_crystal_F_000 392 _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.080 _refine_diff_density_max 0.190 _refine_diff_density_min -0.155 _refine_diff_density_rms 0.039 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 127 _refine_ls_number_reflns 1482 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.081 _refine_ls_R_factor_all 0.0545 _refine_ls_R_factor_gt 0.0445 _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^)+(0.0649P)^2^+0.0671P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1214 _refine_ls_wR_factor_ref 0.1307 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1209 _reflns_number_total 1482 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9ce01344j2.cif _cod_data_source_block oo _cod_database_code 7234393 _shelx_shelxl_version_number 2016/6 _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. ; _shelx_estimated_absorpt_t_min 0.978 _shelx_estimated_absorpt_t_max 0.991 _shelx_res_file ; TITL is183_a.res in P2(1)/c is183.res created by SHELXL-2016/6 at 13:15:30 on 14-Aug-2019 CELL 0.71073 4.763 14.344 12.3505 90 95.601 90 ZERR 4 0.0002 0.0009 0.0007 0 0.005 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H N O UNIT 40 28 4 12 L.S. 4 PLAN 20 BOND $H list 4 fmap 2 acta OMIT 0 50 conf size 0.2 0.1 0.08 temp 20 htab n2 o2 eqiv $1 -x,1-y,1-z htab n2 o3_$1 WGHT 0.064900 0.067100 FVAR 0.73795 O1 4 0.735220 0.290420 0.243314 11.00000 0.05239 0.05568 = 0.03680 -0.00236 0.01098 0.00346 O2 4 0.428320 0.402777 0.209347 11.00000 0.06893 0.06608 = 0.04047 0.01043 0.00764 0.01125 O3 4 0.259816 0.408634 0.537294 11.00000 0.06198 0.05960 = 0.04134 0.00295 0.01659 0.01656 N2 3 0.132508 0.467132 0.371270 11.00000 0.05397 0.05472 = 0.04582 0.00366 0.00966 0.01382 AFIX 93 H2NB 2 0.007655 0.503077 0.395025 11.00000 -1.20000 H2NA 2 0.157675 0.467147 0.303258 11.00000 -1.20000 AFIX 0 C1 1 0.882970 0.227948 0.311940 11.00000 0.03979 0.04288 = 0.04303 -0.00562 0.00664 -0.00395 C2 1 1.072461 0.170475 0.266676 11.00000 0.05084 0.05549 = 0.05078 -0.01546 0.01264 -0.00189 AFIX 43 H2 2 1.098523 0.174719 0.193187 11.00000 -1.20000 AFIX 0 C3 1 1.220831 0.107239 0.332183 11.00000 0.04928 0.05088 = 0.07595 -0.01956 0.01209 0.00472 AFIX 43 H3 2 1.348389 0.067789 0.302721 11.00000 -1.20000 AFIX 0 C4 1 1.184183 0.100957 0.441969 11.00000 0.05469 0.05124 = 0.07068 0.00166 0.00563 0.01065 AFIX 43 H4 2 1.286669 0.057531 0.485565 11.00000 -1.20000 AFIX 0 C5 1 0.995268 0.159277 0.486501 11.00000 0.05058 0.05452 = 0.05091 0.00226 0.01000 0.00658 AFIX 43 H5 2 0.971121 0.155111 0.560164 11.00000 -1.20000 AFIX 0 C6 1 0.840498 0.224429 0.421359 11.00000 0.03915 0.04070 = 0.04334 -0.00327 0.00731 -0.00085 C7 1 0.639806 0.287234 0.459715 11.00000 0.04106 0.04606 = 0.03572 -0.00121 0.00956 -0.00112 AFIX 43 H7 2 0.607621 0.285806 0.532766 11.00000 -1.20000 AFIX 0 C8 1 0.496050 0.348428 0.392913 11.00000 0.03617 0.04008 = 0.03729 -0.00255 0.00647 -0.00238 C9 1 0.541587 0.351723 0.278708 11.00000 0.04266 0.04457 = 0.04154 -0.00130 0.00748 -0.00354 C10 1 0.286081 0.411734 0.439452 11.00000 0.03957 0.03883 = 0.04422 -0.00111 0.00829 -0.00122 HKLF 4 REM is183_a.res in P2(1)/c REM R1 = 0.0445 for 1209 Fo > 4sig(Fo) and 0.0545 for all 1482 data REM 127 parameters refined using 0 restraints END WGHT 0.0649 0.0672 REM Highest difference peak 0.190, deepest hole -0.155, 1-sigma level 0.039 Q1 1 0.6313 0.3563 0.4350 11.00000 0.05 0.15 Q2 1 0.5951 0.2836 0.5602 11.00000 0.05 0.14 Q3 1 1.0095 0.2255 0.4623 11.00000 0.05 0.13 Q4 1 0.9127 0.1733 0.2723 11.00000 0.05 0.13 Q5 1 0.5502 0.4146 0.1228 11.00000 0.05 0.13 Q6 1 0.5530 0.4228 0.2648 11.00000 0.05 0.13 Q7 1 1.0894 0.0902 0.3780 11.00000 0.05 0.12 Q8 1 0.1728 0.5509 0.3594 11.00000 0.05 0.12 Q9 1 0.8118 0.1630 0.4359 11.00000 0.05 0.11 Q10 1 0.4810 0.2945 0.4027 11.00000 0.05 0.11 Q11 1 1.1175 -0.0321 0.3945 11.00000 0.05 0.11 Q12 1 1.4396 0.0409 0.1999 11.00000 0.05 0.11 Q13 1 1.3280 0.0542 0.5377 11.00000 0.05 0.11 Q14 1 0.4330 0.3470 0.6189 11.00000 0.05 0.11 Q15 1 0.2035 0.3293 0.5419 11.00000 0.05 0.10 Q16 1 0.7096 0.0822 0.5570 11.00000 0.05 0.10 Q17 1 0.8588 0.0956 0.5658 11.00000 0.05 0.10 Q18 1 0.8112 0.2072 0.3562 11.00000 0.05 0.10 Q19 1 1.3675 0.1565 0.2160 11.00000 0.05 0.10 Q20 1 0.9859 0.2368 0.0979 11.00000 0.05 0.10 ; _shelx_res_checksum 51592 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -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 _atom_site_refinement_flags_adp O1 O 0.7352(2) 0.29042(9) 0.24331(9) 0.0479(4) Uani 1 1 d . . O2 O 0.4283(3) 0.40278(9) 0.20935(10) 0.0583(4) Uani 1 1 d . . O3 O 0.2598(3) 0.40863(9) 0.53729(10) 0.0535(4) Uani 1 1 d . . N2 N 0.1325(3) 0.46713(11) 0.37127(12) 0.0512(4) Uani 1 1 d . . H2NB H 0.007655 0.503077 0.395025 0.061 Uiso 1 1 calc R U H2NA H 0.157675 0.467147 0.303258 0.061 Uiso 1 1 calc R U C1 C 0.8830(3) 0.22795(12) 0.31194(13) 0.0417(4) Uani 1 1 d . . C2 C 1.0725(4) 0.17047(13) 0.26668(16) 0.0519(5) Uani 1 1 d . . H2 H 1.098523 0.174719 0.193187 0.062 Uiso 1 1 calc R U C3 C 1.2208(4) 0.10724(14) 0.33218(18) 0.0583(6) Uani 1 1 d . . H3 H 1.348389 0.067789 0.302721 0.070 Uiso 1 1 calc R U C4 C 1.1842(4) 0.10096(14) 0.44197(19) 0.0589(6) Uani 1 1 d . . H4 H 1.286669 0.057531 0.485565 0.071 Uiso 1 1 calc R U C5 C 0.9953(4) 0.15928(13) 0.48650(16) 0.0517(5) Uani 1 1 d . . H5 H 0.971121 0.155111 0.560164 0.062 Uiso 1 1 calc R U C6 C 0.8405(3) 0.22443(11) 0.42136(13) 0.0408(4) Uani 1 1 d . . C7 C 0.6398(3) 0.28723(12) 0.45972(13) 0.0406(4) Uani 1 1 d . . H7 H 0.607621 0.285806 0.532766 0.049 Uiso 1 1 calc R U C8 C 0.4960(3) 0.34843(11) 0.39291(13) 0.0377(4) Uani 1 1 d . . C9 C 0.5416(3) 0.35172(12) 0.27871(14) 0.0427(4) Uani 1 1 d . . C10 C 0.2861(3) 0.41173(11) 0.43945(14) 0.0406(4) Uani 1 1 d . . 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 O1 0.0524(7) 0.0557(8) 0.0368(7) -0.0024(5) 0.0110(5) 0.0035(5) O2 0.0689(9) 0.0661(10) 0.0405(8) 0.0104(6) 0.0076(6) 0.0112(6) O3 0.0620(8) 0.0596(9) 0.0413(8) 0.0030(6) 0.0166(6) 0.0166(6) N2 0.0540(9) 0.0547(10) 0.0458(9) 0.0037(7) 0.0097(7) 0.0138(7) C1 0.0398(9) 0.0429(10) 0.0430(9) -0.0056(7) 0.0066(7) -0.0039(7) C2 0.0508(10) 0.0555(12) 0.0508(11) -0.0155(9) 0.0126(8) -0.0019(8) C3 0.0493(11) 0.0509(12) 0.0759(15) -0.0196(10) 0.0121(10) 0.0047(8) C4 0.0547(11) 0.0512(13) 0.0707(14) 0.0017(9) 0.0056(9) 0.0106(8) C5 0.0506(10) 0.0545(12) 0.0509(11) 0.0023(8) 0.0100(8) 0.0066(8) C6 0.0391(8) 0.0407(10) 0.0433(10) -0.0033(7) 0.0073(7) -0.0008(7) C7 0.0411(9) 0.0461(10) 0.0357(9) -0.0012(7) 0.0096(7) -0.0011(7) C8 0.0362(8) 0.0401(10) 0.0373(9) -0.0026(7) 0.0065(7) -0.0024(6) C9 0.0427(9) 0.0446(10) 0.0415(10) -0.0013(7) 0.0075(7) -0.0035(7) C10 0.0396(9) 0.0388(10) 0.0442(10) -0.0011(7) 0.0083(7) -0.0012(7) 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 C9 O1 C1 122.54(13) C10 N2 H2NB 120.0 C10 N2 H2NA 120.0 H2NB N2 H2NA 120.0 O1 C1 C2 117.00(15) O1 C1 C6 120.57(14) C2 C1 C6 122.43(17) C3 C2 C1 118.54(18) C3 C2 H2 120.7 C1 C2 H2 120.7 C2 C3 C4 121.01(17) C2 C3 H3 119.5 C4 C3 H3 119.5 C5 C4 C3 119.93(19) C5 C4 H4 120.0 C3 C4 H4 120.0 C4 C5 C6 120.25(18) C4 C5 H5 119.9 C6 C5 H5 119.9 C1 C6 C5 117.84(16) C1 C6 C7 117.81(15) C5 C6 C7 124.35(16) C8 C7 C6 121.70(15) C8 C7 H7 119.2 C6 C7 H7 119.2 C7 C8 C9 120.19(15) C7 C8 C10 118.47(15) C9 C8 C10 121.34(14) O2 C9 O1 115.29(15) O2 C9 C8 127.51(16) O1 C9 C8 117.20(14) O3 C10 N2 122.98(15) O3 C10 C8 119.28(15) N2 C10 C8 117.72(15) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C9 1.376(2) O1 C1 1.378(2) O2 C9 1.213(2) O3 C10 1.228(2) N2 C10 1.325(2) N2 H2NB 0.8600 N2 H2NA 0.8600 C1 C2 1.380(2) C1 C6 1.387(2) C2 C3 1.366(3) C2 H2 0.9300 C3 C4 1.387(3) C3 H3 0.9300 C4 C5 1.381(3) C4 H4 0.9300 C5 C6 1.396(2) C5 H5 0.9300 C6 C7 1.428(2) C7 C8 1.345(2) C7 H7 0.9300 C8 C9 1.449(2) C8 C10 1.506(2) loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2NA O2 0.86 2.04 2.7178(19) 135.4 . N2 H2NB O3 0.86 2.03 2.8904(19) 174.6 3_566 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 C9 O1 C1 C2 -179.65(13) C9 O1 C1 C6 0.1(2) O1 C1 C2 C3 -179.50(15) C6 C1 C2 C3 0.7(3) C1 C2 C3 C4 -0.4(3) C2 C3 C4 C5 0.0(3) C3 C4 C5 C6 0.1(3) O1 C1 C6 C5 179.62(14) C2 C1 C6 C5 -0.6(2) O1 C1 C6 C7 0.1(2) C2 C1 C6 C7 179.84(15) C4 C5 C6 C1 0.2(3) C4 C5 C6 C7 179.68(16) C1 C6 C7 C8 -0.3(2) C5 C6 C7 C8 -179.79(15) C6 C7 C8 C9 0.3(2) C6 C7 C8 C10 179.45(14) C1 O1 C9 O2 179.79(14) C1 O1 C9 C8 -0.1(2) C7 C8 C9 O2 -179.98(16) C10 C8 C9 O2 0.9(3) C7 C8 C9 O1 -0.1(2) C10 C8 C9 O1 -179.22(13) C7 C8 C10 O3 2.9(2) C9 C8 C10 O3 -177.88(15) C7 C8 C10 N2 -175.51(15) C9 C8 C10 N2 3.7(2)