#------------------------------------------------------------------------------ #$Date: 2019-10-05 03:37:53 +0300 (Sat, 05 Oct 2019) $ #$Revision: 219101 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/23/43/7234392.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_7234392 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 H8 N2 O2' _chemical_formula_weight 188.18 _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 93.970(14) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 4.7260(9) _cell_length_b 14.633(3) _cell_length_c 12.5056(17) _cell_measurement_reflns_used 402 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 20.613 _cell_measurement_theta_min 4.279 _cell_volume 862.8(3) _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 0.1083 _diffrn_reflns_av_unetI/netI 0.1236 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 8503 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 29.996 _diffrn_reflns_theta_min 3.228 _diffrn_source 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.32968 _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 colorless _exptl_crystal_density_diffrn 1.449 _exptl_crystal_description stick _exptl_crystal_F_000 392 _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.040 _exptl_crystal_size_min 0.040 _refine_diff_density_max 0.464 _refine_diff_density_min -0.228 _refine_diff_density_rms 0.069 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.874 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 127 _refine_ls_number_reflns 2528 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.874 _refine_ls_R_factor_all 0.2195 _refine_ls_R_factor_gt 0.0879 _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^)+(0.1074P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2096 _refine_ls_wR_factor_ref 0.2744 _reflns_Friedel_coverage 0.000 _reflns_number_gt 804 _reflns_number_total 2528 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9ce01344j2.cif _cod_data_source_block on _cod_original_cell_volume 862.7(3) _cod_database_code 7234392 _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 0.980 _shelx_estimated_absorpt_t_max 0.996 _shelx_res_file ; TITL is90_a.res in P2(1)/c is90.res created by SHELXL-2016/6 at 18:53:54 on 30-Jul-2019 CELL 0.71073 4.726 14.6328 12.5056 90 93.97 90 ZERR 4 0.0009 0.0027 0.0017 0 0.014 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H N O UNIT 40 32 8 8 L.S. 10 PLAN 20 acta BOND $H FMAP 2 list 4 OMIT 0 60 conf size 0.2 0.04 0.04 temp 20 htab n2 n1 eqiv $1 -x,1-y,1-z htab n2 o3_$1 WGHT 0.107400 FVAR 0.69327 O1 4 0.733495 0.289707 0.236871 11.00000 0.07351 0.06312 = 0.05240 -0.00044 0.01408 0.00502 O3 4 0.257096 0.407332 0.533253 11.00000 0.07984 0.07112 = 0.05889 0.00448 0.01718 0.01861 N1 3 0.411610 0.403104 0.205424 11.00000 0.08354 0.07046 = 0.05401 0.00586 0.00761 0.01016 AFIX 83 H1N 2 0.434677 0.385134 0.144532 11.00000 -1.20000 AFIX 0 N2 3 0.134163 0.467328 0.372027 11.00000 0.07563 0.06770 = 0.06096 0.00185 0.01269 0.01674 AFIX 93 H2NB 2 0.012045 0.503330 0.397729 11.00000 -1.20000 H2NA 2 0.158799 0.467976 0.304537 11.00000 -1.20000 AFIX 0 C1 1 0.878021 0.228184 0.303617 11.00000 0.05890 0.04896 = 0.05033 -0.00277 0.00241 0.00159 C2 1 1.065342 0.170007 0.256877 11.00000 0.06488 0.06389 = 0.06059 -0.01181 0.00871 -0.00152 AFIX 43 H2 2 1.093030 0.173739 0.184101 11.00000 -1.20000 AFIX 0 C3 1 1.208011 0.107103 0.320611 11.00000 0.06233 0.05592 = 0.07812 -0.01460 0.00704 0.00618 AFIX 43 H3 2 1.335012 0.067763 0.290482 11.00000 -1.20000 AFIX 0 C4 1 1.168685 0.100434 0.428248 11.00000 0.07049 0.05500 = 0.07143 -0.00543 -0.00148 0.00439 AFIX 43 H4 2 1.266735 0.056733 0.470175 11.00000 -1.20000 AFIX 0 C5 1 0.981370 0.159513 0.473683 11.00000 0.06364 0.06536 = 0.06361 -0.00090 0.01077 0.00610 AFIX 43 H5 2 0.954608 0.155348 0.546501 11.00000 -1.20000 AFIX 0 C6 1 0.832842 0.225022 0.411500 11.00000 0.04856 0.05255 = 0.05550 -0.00210 0.00346 -0.00393 C7 1 0.634779 0.288570 0.450835 11.00000 0.05530 0.05553 = 0.04993 0.00232 0.00979 -0.00187 AFIX 43 H7 2 0.603909 0.288071 0.523475 11.00000 -1.20000 AFIX 0 C8 1 0.492636 0.348554 0.387158 11.00000 0.05055 0.04706 = 0.04609 -0.00092 0.00739 -0.00018 C9 1 0.536889 0.349257 0.273073 11.00000 0.05444 0.05518 = 0.05188 -0.00243 0.00609 -0.00636 C10 1 0.284189 0.410925 0.436339 11.00000 0.05889 0.04561 = 0.06040 -0.00067 0.01277 0.00136 HKLF 4 REM is90_a.res in P2(1)/c REM R1 = 0.0879 for 804 Fo > 4sig(Fo) and 0.2195 for all 2528 data REM 127 parameters refined using 0 restraints END WGHT 0.1067 0.0000 REM Highest difference peak 0.464, deepest hole -0.228, 1-sigma level 0.069 Q1 1 0.0910 0.4714 0.4842 11.00000 0.05 0.37 Q2 1 0.5869 0.2833 0.5555 11.00000 0.05 0.32 Q3 1 1.3057 0.0418 0.5031 11.00000 0.05 0.28 Q4 1 0.7311 0.2827 0.1320 11.00000 0.05 0.27 Q5 1 1.1197 0.1751 0.1559 11.00000 0.05 0.26 Q6 1 -0.0442 0.5349 0.4104 11.00000 0.05 0.24 Q7 1 0.3788 0.3525 0.6006 11.00000 0.05 0.24 Q8 1 -0.0183 0.5326 0.3193 11.00000 0.05 0.23 Q9 1 1.3769 0.1609 0.2109 11.00000 0.05 0.22 Q10 1 0.4504 0.3477 0.4996 11.00000 0.05 0.22 Q11 1 0.4488 0.4843 0.1536 11.00000 0.05 0.21 Q12 1 0.2095 0.4082 0.6442 11.00000 0.05 0.20 Q13 1 0.1954 0.3311 0.3692 11.00000 0.05 0.20 Q14 1 0.9337 0.1512 0.5808 11.00000 0.05 0.19 Q15 1 1.3152 0.1635 0.4949 11.00000 0.05 0.18 Q16 1 1.4101 0.0476 0.2716 11.00000 0.05 0.18 Q17 1 0.9915 0.2792 0.4792 11.00000 0.05 0.17 Q18 1 0.6808 0.2874 0.3400 11.00000 0.05 0.17 Q19 1 0.5017 0.4192 0.1451 11.00000 0.05 0.16 Q20 1 1.4455 0.0449 0.1756 11.00000 0.05 0.16 ; _shelx_res_checksum 19252 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 0.7335(5) 0.28971(16) 0.23687(18) 0.0626(7) Uani 1 1 d . . O3 O 0.2571(5) 0.40733(16) 0.5333(2) 0.0694(8) Uani 1 1 d . . N1 N 0.4116(7) 0.4031(2) 0.2054(3) 0.0692(9) Uani 1 1 d . . H1N H 0.434677 0.385134 0.144532 0.083 Uiso 1 1 calc R U N2 N 0.1342(6) 0.4673(2) 0.3720(3) 0.0677(9) Uani 1 1 d . . H2NB H 0.012045 0.503330 0.397729 0.081 Uiso 1 1 calc R U H2NA H 0.158799 0.467976 0.304537 0.081 Uiso 1 1 calc R U C1 C 0.8780(7) 0.2282(2) 0.3036(3) 0.0528(8) Uani 1 1 d . . C2 C 1.0653(7) 0.1700(2) 0.2569(3) 0.0629(10) Uani 1 1 d . . H2 H 1.093030 0.173739 0.184101 0.075 Uiso 1 1 calc R U C3 C 1.2080(8) 0.1071(2) 0.3206(3) 0.0654(10) Uani 1 1 d . . H3 H 1.335012 0.067763 0.290482 0.078 Uiso 1 1 calc R U C4 C 1.1687(8) 0.1004(2) 0.4282(3) 0.0659(10) Uani 1 1 d . . H4 H 1.266735 0.056733 0.470175 0.079 Uiso 1 1 calc R U C5 C 0.9814(7) 0.1595(2) 0.4737(3) 0.0639(10) Uani 1 1 d . . H5 H 0.954608 0.155348 0.546501 0.077 Uiso 1 1 calc R U C6 C 0.8328(6) 0.2250(2) 0.4115(3) 0.0522(8) Uani 1 1 d . . C7 C 0.6348(6) 0.2886(2) 0.4508(3) 0.0533(8) Uani 1 1 d . . H7 H 0.603909 0.288071 0.523475 0.064 Uiso 1 1 calc R U C8 C 0.4926(6) 0.3486(2) 0.3872(3) 0.0477(8) Uani 1 1 d . . C9 C 0.5369(7) 0.3493(2) 0.2731(3) 0.0537(9) Uani 1 1 d . . C10 C 0.2842(7) 0.4109(2) 0.4363(3) 0.0546(9) 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 0.0735(15) 0.0631(15) 0.0524(14) -0.0004(12) 0.0141(12) 0.0050(12) O3 0.0798(18) 0.0711(17) 0.0589(16) 0.0045(13) 0.0172(13) 0.0186(13) N1 0.084(2) 0.070(2) 0.0540(19) 0.0059(15) 0.0076(17) 0.0102(16) N2 0.0756(19) 0.068(2) 0.0610(19) 0.0018(16) 0.0127(16) 0.0167(17) C1 0.059(2) 0.0490(19) 0.0503(19) -0.0028(15) 0.0024(16) 0.0016(16) C2 0.065(2) 0.064(2) 0.061(2) -0.0118(19) 0.0087(19) -0.0015(18) C3 0.062(2) 0.056(2) 0.078(3) -0.015(2) 0.007(2) 0.0062(17) C4 0.070(2) 0.055(2) 0.071(3) -0.0054(19) -0.001(2) 0.0044(17) C5 0.064(2) 0.065(2) 0.064(2) -0.0009(18) 0.0108(18) 0.0061(19) C6 0.0486(18) 0.053(2) 0.055(2) -0.0021(16) 0.0035(16) -0.0039(16) C7 0.0553(18) 0.0555(19) 0.0499(19) 0.0023(16) 0.0098(16) -0.0019(16) C8 0.0505(17) 0.0471(18) 0.0461(18) -0.0009(14) 0.0074(15) -0.0002(14) C9 0.054(2) 0.055(2) 0.052(2) -0.0024(16) 0.0061(17) -0.0064(16) C10 0.059(2) 0.0456(19) 0.060(2) -0.0007(16) 0.0128(18) 0.0014(15) 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 122.3(3) C9 N1 H1N 109.5 C10 N2 H2NB 120.0 C10 N2 H2NA 120.0 H2NB N2 H2NA 120.0 O1 C1 C6 120.7(3) O1 C1 C2 116.8(3) C6 C1 C2 122.5(3) C3 C2 C1 118.2(3) C3 C2 H2 120.9 C1 C2 H2 120.9 C2 C3 C4 121.7(3) C2 C3 H3 119.2 C4 C3 H3 119.2 C3 C4 C5 119.4(4) C3 C4 H4 120.3 C5 C4 H4 120.3 C4 C5 C6 120.8(4) C4 C5 H5 119.6 C6 C5 H5 119.6 C1 C6 C5 117.5(3) C1 C6 C7 117.6(3) C5 C6 C7 124.9(3) C8 C7 C6 122.4(3) C8 C7 H7 118.8 C6 C7 H7 118.8 C7 C8 C9 119.3(3) C7 C8 C10 118.1(3) C9 C8 C10 122.6(3) N1 C9 O1 117.9(3) N1 C9 C8 124.3(3) O1 C9 C8 117.7(3) O3 C10 N2 122.6(3) O3 C10 C8 119.5(3) N2 C10 C8 117.9(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C9 1.373(4) O1 C1 1.377(4) O3 C10 1.229(4) N1 C9 1.272(4) N1 H1N 0.8200 N2 C10 1.324(4) N2 H2NB 0.8600 N2 H2NA 0.8600 C1 C6 1.381(5) C1 C2 1.386(4) C2 C3 1.365(5) C2 H2 0.9300 C3 C4 1.375(5) C3 H3 0.9300 C4 C5 1.387(5) C4 H4 0.9300 C5 C6 1.393(5) C5 H5 0.9300 C6 C7 1.431(4) C7 C8 1.335(4) C7 H7 0.9300 C8 C9 1.456(4) C8 C10 1.505(4) 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 N1 0.86 2.02 2.706(4) 136.4 . N2 H2NB O3 0.86 2.06 2.914(4) 175.9 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 C6 -1.0(4) C9 O1 C1 C2 178.3(3) O1 C1 C2 C3 -178.8(3) C6 C1 C2 C3 0.4(5) C1 C2 C3 C4 0.3(5) C2 C3 C4 C5 -0.6(6) C3 C4 C5 C6 0.2(5) O1 C1 C6 C5 178.5(3) C2 C1 C6 C5 -0.8(5) O1 C1 C6 C7 -0.9(4) C2 C1 C6 C7 179.9(3) C4 C5 C6 C1 0.5(5) C4 C5 C6 C7 179.7(3) C1 C6 C7 C8 1.0(5) C5 C6 C7 C8 -178.3(3) C6 C7 C8 C9 0.7(5) C6 C7 C8 C10 178.6(3) C1 O1 C9 N1 -179.3(3) C1 O1 C9 C8 2.7(4) C7 C8 C9 N1 179.6(3) C10 C8 C9 N1 1.8(5) C7 C8 C9 O1 -2.5(4) C10 C8 C9 O1 179.7(3) C7 C8 C10 O3 2.4(5) C9 C8 C10 O3 -179.7(3) C7 C8 C10 N2 -176.9(3) C9 C8 C10 N2 0.9(5)