#------------------------------------------------------------------------------ #$Date: 2019-10-05 03:37:53 +0300 (Sat, 05 Oct 2019) $ #$Revision: 219101 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/23/43/7234394.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_7234394 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 O2 S' _chemical_formula_weight 205.23 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 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 100.689(8) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 11.3493(10) _cell_length_b 5.6476(4) _cell_length_c 14.2419(10) _cell_measurement_reflns_used 1011 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 25.396 _cell_measurement_theta_min 3.873 _cell_volume 897.01(12) _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 0.998 _diffrn_measured_fraction_theta_max 0.998 _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 0.0621 _diffrn_reflns_av_unetI/netI 0.0525 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 5549 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 24.985 _diffrn_reflns_theta_max 24.985 _diffrn_reflns_theta_min 3.654 _diffrn_source 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.328 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.01614 _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 yellow _exptl_crystal_density_diffrn 1.520 _exptl_crystal_description plate _exptl_crystal_F_000 424 _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.140 _exptl_crystal_size_min 0.040 _refine_diff_density_max 0.270 _refine_diff_density_min -0.284 _refine_diff_density_rms 0.065 _refine_ls_extinction_coef 0.011(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2016/6 (Sheldrick 2016)' _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 128 _refine_ls_number_reflns 1576 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.033 _refine_ls_R_factor_all 0.0646 _refine_ls_R_factor_gt 0.0502 _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^)+(0.0783P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1296 _refine_ls_wR_factor_ref 0.1466 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1198 _reflns_number_total 1576 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9ce01344j2.cif _cod_data_source_block so _cod_database_code 7234394 _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 0.937 _shelx_estimated_absorpt_t_max 0.987 _shelx_res_file ; TITL is137_a.res in P2(1)/n is137.res created by SHELXL-2016/6 at 16:50:19 on 30-Jul-2019 CELL 0.71073 11.3493 5.6476 14.2419 90 100.689 90 ZERR 4 0.001 0.0004 0.001 0 0.008 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H N O S UNIT 40 28 4 8 4 L.S. 4 PLAN 20 BOND $H list 4 fmap 2 acta OMIT 0 50 conf size 0.2 0.14 0.04 temp 20 htab n2 o2 eqiv $1 1-x,1-y,2-z htab n2 s1_$1 WGHT 0.078300 EXTI 0.011333 FVAR 0.74943 S1 5 0.393709 0.696432 0.877427 11.00000 0.07161 0.05455 = 0.04214 -0.00400 0.01659 0.01023 O1 4 0.443417 0.199515 0.581713 11.00000 0.06045 0.05115 = 0.04331 -0.00735 0.01162 0.00975 O2 4 0.532764 0.066950 0.720339 11.00000 0.08314 0.05919 = 0.05033 -0.00094 0.01469 0.02188 N2 3 0.507302 0.295205 0.879417 11.00000 0.09180 0.05962 = 0.04109 -0.00474 0.01051 0.02515 AFIX 93 H2NA 2 0.532539 0.174084 0.852342 11.00000 -1.20000 H2NB 2 0.522703 0.308103 0.940641 11.00000 -1.20000 AFIX 0 C8 1 0.421812 0.426713 0.721452 11.00000 0.04419 0.04753 = 0.03998 -0.00501 0.01411 -0.00076 C7 1 0.354627 0.585465 0.663503 11.00000 0.04752 0.04378 = 0.04486 -0.00619 0.01555 0.00050 AFIX 43 H7 2 0.323930 0.716209 0.690561 11.00000 -1.20000 AFIX 0 C6 1 0.329540 0.558182 0.562252 11.00000 0.04386 0.04686 = 0.04306 -0.00284 0.01280 -0.00201 C1 1 0.375179 0.362354 0.523319 11.00000 0.04311 0.04918 = 0.04435 -0.00258 0.01050 -0.00400 C10 1 0.445167 0.460680 0.827203 11.00000 0.04859 0.04841 = 0.04342 0.00092 0.01408 -0.00035 C9 1 0.470094 0.223281 0.679026 11.00000 0.04979 0.05152 = 0.04507 -0.00612 0.01447 -0.00110 C2 1 0.355776 0.317723 0.425829 11.00000 0.05413 0.06241 = 0.04874 -0.01285 0.01261 -0.00438 AFIX 43 H2 2 0.388400 0.185437 0.401331 11.00000 -1.20000 AFIX 0 C3 1 0.286125 0.477668 0.366825 11.00000 0.05831 0.07340 = 0.03977 -0.00556 0.01081 -0.00347 AFIX 43 H3 2 0.271333 0.452167 0.301174 11.00000 -1.20000 AFIX 0 C5 1 0.258926 0.714946 0.499424 11.00000 0.05803 0.05858 = 0.04981 0.00021 0.01481 0.00533 AFIX 43 H5 2 0.226021 0.847611 0.523415 11.00000 -1.20000 AFIX 0 C4 1 0.237865 0.674430 0.402703 11.00000 0.05721 0.07087 = 0.04571 0.00787 0.00918 0.00623 AFIX 43 H4 2 0.191075 0.779655 0.361429 11.00000 -1.20000 AFIX 0 HKLF 4 REM is137_a.res in P2(1)/n REM R1 = 0.0502 for 1198 Fo > 4sig(Fo) and 0.0646 for all 1576 data REM 128 parameters refined using 0 restraints END WGHT 0.0783 0.0000 REM Highest difference peak 0.270, deepest hole -0.284, 1-sigma level 0.065 Q1 1 0.3043 0.1391 0.6190 11.00000 0.05 0.19 Q2 1 0.4009 0.9162 0.8790 11.00000 0.05 0.18 Q3 1 0.3783 0.0517 0.5249 11.00000 0.05 0.18 Q4 1 0.4207 -0.0725 0.7369 11.00000 0.05 0.18 Q5 1 0.4634 0.6087 0.5988 11.00000 0.05 0.18 Q6 1 0.3804 0.2608 0.7763 11.00000 0.05 0.17 Q7 1 0.0779 0.7116 0.4374 11.00000 0.05 0.17 Q8 1 0.4531 0.1539 0.8403 11.00000 0.05 0.17 Q9 1 0.3407 0.4445 0.4014 11.00000 0.05 0.17 Q10 1 0.3278 0.8707 0.5508 11.00000 0.05 0.16 Q11 1 0.0288 0.7576 0.3183 11.00000 0.05 0.16 Q12 1 0.4676 0.8316 0.9369 11.00000 0.05 0.16 Q13 1 0.4604 -0.0333 0.6731 11.00000 0.05 0.16 Q14 1 0.3574 0.4942 0.6760 11.00000 0.05 0.16 Q15 1 0.4432 0.3393 0.8460 11.00000 0.05 0.16 Q16 1 0.5161 0.6621 0.9407 11.00000 0.05 0.15 Q17 1 0.2783 1.1303 0.5220 11.00000 0.05 0.15 Q18 1 0.3981 0.6957 0.6205 11.00000 0.05 0.15 Q19 1 0.4723 0.6640 0.6811 11.00000 0.05 0.15 Q20 1 0.5376 -0.0388 0.9348 11.00000 0.05 0.15 ; _shelx_res_checksum 17144 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -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 S1 S 0.39371(6) 0.69643(13) 0.87743(4) 0.0553(3) Uani 1 1 d . . O1 O 0.44342(15) 0.1995(3) 0.58171(12) 0.0514(5) Uani 1 1 d . . O2 O 0.53276(18) 0.0669(4) 0.72034(12) 0.0639(6) Uani 1 1 d . . N2 N 0.5073(2) 0.2952(4) 0.87942(17) 0.0644(7) Uani 1 1 d . . H2NA H 0.532539 0.174084 0.852342 0.077 Uiso 1 1 calc R U H2NB H 0.522703 0.308103 0.940641 0.077 Uiso 1 1 calc R U C8 C 0.42181(19) 0.4267(4) 0.72145(15) 0.0431(6) Uani 1 1 d . . C7 C 0.3546(2) 0.5855(5) 0.66350(16) 0.0445(6) Uani 1 1 d . . H7 H 0.323930 0.716209 0.690561 0.053 Uiso 1 1 calc R U C6 C 0.3295(2) 0.5582(5) 0.56225(16) 0.0440(6) Uani 1 1 d . . C1 C 0.3752(2) 0.3624(5) 0.52332(17) 0.0452(6) Uani 1 1 d . . C10 C 0.4452(2) 0.4607(5) 0.82720(16) 0.0461(6) Uani 1 1 d . . C9 C 0.4701(2) 0.2233(5) 0.67903(19) 0.0481(6) Uani 1 1 d . . C2 C 0.3558(2) 0.3177(5) 0.42583(19) 0.0547(7) Uani 1 1 d . . H2 H 0.388400 0.185437 0.401331 0.066 Uiso 1 1 calc R U C3 C 0.2861(2) 0.4777(6) 0.36682(18) 0.0569(7) Uani 1 1 d . . H3 H 0.271333 0.452167 0.301174 0.068 Uiso 1 1 calc R U C5 C 0.2589(2) 0.7149(5) 0.4994(2) 0.0549(7) Uani 1 1 d . . H5 H 0.226021 0.847611 0.523415 0.066 Uiso 1 1 calc R U C4 C 0.2379(3) 0.6744(5) 0.40270(19) 0.0580(8) Uani 1 1 d . . H4 H 0.191075 0.779655 0.361429 0.070 Uiso 1 1 calc R U 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 S1 0.0716(5) 0.0546(5) 0.0421(5) -0.0040(3) 0.0166(4) 0.0102(3) O1 0.0604(11) 0.0511(12) 0.0433(10) -0.0074(8) 0.0116(8) 0.0097(8) O2 0.0831(13) 0.0592(13) 0.0503(10) -0.0009(9) 0.0147(9) 0.0219(10) N2 0.0918(17) 0.0596(16) 0.0411(12) -0.0047(10) 0.0105(12) 0.0252(13) C8 0.0442(13) 0.0475(15) 0.0400(12) -0.0050(10) 0.0141(10) -0.0008(11) C7 0.0475(13) 0.0438(14) 0.0449(13) -0.0062(11) 0.0156(11) 0.0005(11) C6 0.0439(12) 0.0469(15) 0.0431(12) -0.0028(10) 0.0128(10) -0.0020(10) C1 0.0431(13) 0.0492(15) 0.0444(13) -0.0026(11) 0.0105(11) -0.0040(11) C10 0.0486(13) 0.0484(15) 0.0434(12) 0.0009(11) 0.0141(11) -0.0004(11) C9 0.0498(14) 0.0515(16) 0.0451(15) -0.0061(11) 0.0145(12) -0.0011(12) C2 0.0541(15) 0.062(2) 0.0487(15) -0.0129(12) 0.0126(12) -0.0044(12) C3 0.0583(16) 0.073(2) 0.0398(13) -0.0056(13) 0.0108(12) -0.0035(14) C5 0.0580(16) 0.0586(19) 0.0498(15) 0.0002(12) 0.0148(13) 0.0053(13) C4 0.0572(16) 0.071(2) 0.0457(16) 0.0079(13) 0.0092(13) 0.0062(13) 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' S S 0.1246 0.1234 '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 122.7(2) C10 N2 H2NA 120.0 C10 N2 H2NB 120.0 H2NA N2 H2NB 120.0 C7 C8 C9 118.9(2) C7 C8 C10 120.3(2) C9 C8 C10 120.8(2) C8 C7 C6 122.0(2) C8 C7 H7 119.0 C6 C7 H7 119.0 C1 C6 C5 117.6(2) C1 C6 C7 118.3(2) C5 C6 C7 124.1(2) O1 C1 C6 120.2(2) O1 C1 C2 116.7(2) C6 C1 C2 123.1(2) N2 C10 C8 117.1(2) N2 C10 S1 121.24(19) C8 C10 S1 121.65(18) O2 C9 O1 114.7(2) O2 C9 C8 127.3(2) O1 C9 C8 118.0(2) C3 C2 C1 117.2(3) C3 C2 H2 121.4 C1 C2 H2 121.4 C4 C3 C2 121.6(2) C4 C3 H3 119.2 C2 C3 H3 119.2 C4 C5 C6 120.5(3) C4 C5 H5 119.7 C6 C5 H5 119.7 C5 C4 C3 119.9(3) C5 C4 H4 120.0 C3 C4 H4 120.0 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance S1 C10 1.667(3) O1 C9 1.369(3) O1 C1 1.378(3) O2 C9 1.215(3) N2 C10 1.315(3) N2 H2NA 0.8600 N2 H2NB 0.8600 C8 C7 1.354(3) C8 C9 1.452(4) C8 C10 1.492(3) C7 C6 1.425(3) C7 H7 0.9300 C6 C1 1.380(3) C6 C5 1.400(4) C1 C2 1.388(3) C2 C3 1.379(4) C2 H2 0.9300 C3 C4 1.378(4) C3 H3 0.9300 C5 C4 1.373(4) C5 H5 0.9300 C4 H4 0.9300 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 1.98 2.669(3) 136.9 . N2 H2NB S1 0.86 2.59 3.437(2) 169.0 3_667 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 C8 C7 C6 0.3(4) C10 C8 C7 C6 -179.5(2) C8 C7 C6 C1 0.4(4) C8 C7 C6 C5 178.8(2) C9 O1 C1 C6 -0.6(3) C9 O1 C1 C2 179.5(2) C5 C6 C1 O1 -178.8(2) C7 C6 C1 O1 -0.2(3) C5 C6 C1 C2 1.1(4) C7 C6 C1 C2 179.7(2) C7 C8 C10 N2 177.5(2) C9 C8 C10 N2 -2.3(4) C7 C8 C10 S1 -1.9(3) C9 C8 C10 S1 178.38(19) C1 O1 C9 O2 -178.9(2) C1 O1 C9 C8 1.3(3) C7 C8 C9 O2 179.1(3) C10 C8 C9 O2 -1.2(4) C7 C8 C9 O1 -1.1(4) C10 C8 C9 O1 178.7(2) O1 C1 C2 C3 179.1(2) C6 C1 C2 C3 -0.8(4) C1 C2 C3 C4 0.2(4) C1 C6 C5 C4 -0.8(4) C7 C6 C5 C4 -179.2(2) C6 C5 C4 C3 0.2(4) C2 C3 C4 C5 0.1(5)