#------------------------------------------------------------------------------ #$Date: 2019-10-05 03:37:53 +0300 (Sat, 05 Oct 2019) $ #$Revision: 219101 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/23/43/7234391.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_7234391 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 O S' _chemical_formula_weight 204.24 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -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 73.758(15) _cell_angle_beta 69.604(16) _cell_angle_gamma 68.658(15) _cell_formula_units_Z 2 _cell_length_a 7.3622(12) _cell_length_b 7.8278(13) _cell_length_c 9.5248(18) _cell_measurement_reflns_used 437 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 23.015 _cell_measurement_theta_min 3.528 _cell_volume 471.81(16) _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 0.0642 _diffrn_reflns_av_unetI/netI 0.0889 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 3091 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 24.997 _diffrn_reflns_theta_max 24.997 _diffrn_reflns_theta_min 3.091 _diffrn_source 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.307 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.04158 _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 1.438 _exptl_crystal_description stick _exptl_crystal_F_000 212 _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.050 _exptl_crystal_size_min 0.040 _refine_diff_density_max 0.262 _refine_diff_density_min -0.322 _refine_diff_density_rms 0.080 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.985 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 127 _refine_ls_number_reflns 1654 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.985 _refine_ls_R_factor_all 0.1021 _refine_ls_R_factor_gt 0.0718 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0803P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1636 _refine_ls_wR_factor_ref 0.1898 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1015 _reflns_number_total 1654 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9ce01344j2.cif _cod_data_source_block sn _cod_database_code 7234391 _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 0.941 _shelx_estimated_absorpt_t_max 0.988 _shelx_res_file ; TITL is167_a.res in P-1 is167.res created by SHELXL-2016/6 at 19:05:43 on 30-Jul-2019 CELL 0.71073 7.3622 7.8278 9.5248 73.758 69.604 68.658 ZERR 2 0.0012 0.0013 0.0018 0.015 0.016 0.015 LATT 1 SFAC C H N O S UNIT 20 16 4 2 2 L.S. 4 PLAN 20 list 4 acta OMIT 0 50 conf size 0.2 0.05 0.04 temp 20 htab n2 n1 eqiv $1 1-x,-y,2-z htab n2 s1_$1 WGHT 0.080300 FVAR 0.89638 S1 5 0.695202 0.010033 0.746276 11.00000 0.08955 0.04420 = 0.08249 -0.00759 -0.01208 -0.02395 O1 4 0.623789 0.717759 0.572132 11.00000 0.07664 0.04569 = 0.05657 -0.00433 -0.01664 -0.01971 N1 3 0.448631 0.628034 0.811055 11.00000 0.08754 0.05049 = 0.05914 -0.01498 -0.00698 -0.01442 AFIX 83 H1N 2 0.426279 0.739850 0.805921 11.00000 -1.20000 AFIX 0 N2 3 0.480736 0.270270 0.910370 11.00000 0.09324 0.05557 = 0.05730 -0.00235 -0.00997 -0.03022 AFIX 93 H2NA 2 0.434678 0.384175 0.923750 11.00000 -1.20000 H2NB 2 0.448065 0.183933 0.983699 11.00000 -1.20000 AFIX 0 C1 1 0.753605 0.682338 0.431844 11.00000 0.05257 0.05537 = 0.04969 -0.00002 -0.01793 -0.01898 C2 1 0.803770 0.833763 0.329650 11.00000 0.07967 0.06338 = 0.07001 0.00971 -0.02551 -0.02871 AFIX 43 H2 2 0.753620 0.951746 0.355413 11.00000 -1.20000 AFIX 0 C3 1 0.931344 0.802198 0.187938 11.00000 0.08177 0.08280 = 0.08040 0.02498 -0.02636 -0.03579 AFIX 43 H3 2 0.965499 0.901588 0.115618 11.00000 -1.20000 AFIX 0 C4 1 1.009348 0.626569 0.151127 11.00000 0.06489 0.11178 = 0.06127 0.00583 -0.01107 -0.03102 AFIX 43 H4 2 1.096778 0.608677 0.055192 11.00000 -1.20000 AFIX 0 C5 1 0.958958 0.477052 0.255249 11.00000 0.05762 0.08372 = 0.06002 -0.00884 -0.01144 -0.01542 AFIX 43 H5 2 1.010139 0.359043 0.229432 11.00000 -1.20000 AFIX 0 C6 1 0.829617 0.504852 0.400593 11.00000 0.04193 0.05248 = 0.05565 -0.00451 -0.01623 -0.00974 C7 1 0.774264 0.357008 0.519238 11.00000 0.04839 0.04478 = 0.06028 -0.01276 -0.01648 -0.00912 AFIX 43 H7 2 0.826775 0.235844 0.499775 11.00000 -1.20000 AFIX 0 C8 1 0.649393 0.388241 0.657003 11.00000 0.04533 0.04304 = 0.05396 -0.00995 -0.01523 -0.01254 C9 1 0.567491 0.579946 0.685870 11.00000 0.05470 0.04126 = 0.05355 -0.00555 -0.01791 -0.01278 C10 1 0.600973 0.228168 0.777947 11.00000 0.05622 0.04676 = 0.05339 -0.00284 -0.01634 -0.02150 HKLF 4 REM is167_a.res in P-1 REM R1 = 0.0718 for 1015 Fo > 4sig(Fo) and 0.1021 for all 1654 data REM 127 parameters refined using 0 restraints END WGHT 0.0801 0.0000 REM Highest difference peak 0.262, deepest hole -0.322, 1-sigma level 0.080 Q1 1 0.5874 -0.0743 0.7681 11.00000 0.05 0.26 Q2 1 0.7741 0.0023 0.5997 11.00000 0.05 0.26 Q3 1 0.5824 0.7314 0.8017 11.00000 0.05 0.25 Q4 1 0.7457 1.0244 0.5193 11.00000 0.05 0.25 Q5 1 0.6973 0.3726 0.5335 11.00000 0.05 0.25 Q6 1 0.7493 0.8292 0.5799 11.00000 0.05 0.24 Q7 1 1.1605 0.9849 0.1194 11.00000 0.05 0.21 Q8 1 1.0199 0.9572 0.1609 11.00000 0.05 0.20 Q9 1 0.9702 0.5895 -0.0153 11.00000 0.05 0.20 Q10 1 0.5959 0.3062 0.7095 11.00000 0.05 0.20 Q11 1 0.8149 0.7949 0.3853 11.00000 0.05 0.19 Q12 1 0.6439 0.7261 0.6574 11.00000 0.05 0.19 Q13 1 0.6075 0.3419 0.6790 11.00000 0.05 0.19 Q14 1 0.8139 0.4140 0.2559 11.00000 0.05 0.18 Q15 1 0.5336 0.2912 0.6558 11.00000 0.05 0.18 Q16 1 0.6899 0.7833 0.2666 11.00000 0.05 0.18 Q17 1 0.4634 0.5934 0.9317 11.00000 0.05 0.18 Q18 1 0.4915 0.6636 0.5429 11.00000 0.05 0.18 Q19 1 0.7959 0.3654 0.4067 11.00000 0.05 0.17 Q20 1 0.6393 0.0182 0.8777 11.00000 0.05 0.17 ; _shelx_res_checksum 88791 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' 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 0.69520(17) 0.01003(13) 0.74628(12) 0.0749(5) Uani 1 1 d . . O1 O 0.6238(4) 0.7178(3) 0.5721(3) 0.0607(7) Uani 1 1 d . . N1 N 0.4486(5) 0.6280(4) 0.8111(3) 0.0700(10) Uani 1 1 d . . H1N H 0.426279 0.739850 0.805921 0.084 Uiso 1 1 calc R U N2 N 0.4807(5) 0.2703(5) 0.9104(3) 0.0710(10) Uani 1 1 d . . H2NA H 0.434678 0.384175 0.923750 0.085 Uiso 1 1 calc R U H2NB H 0.448065 0.183933 0.983699 0.085 Uiso 1 1 calc R U C1 C 0.7536(5) 0.6823(5) 0.4318(4) 0.0526(9) Uani 1 1 d . . C2 C 0.8038(6) 0.8338(6) 0.3297(5) 0.0721(12) Uani 1 1 d . . H2 H 0.753620 0.951746 0.355413 0.087 Uiso 1 1 calc R U C3 C 0.9313(7) 0.8022(7) 0.1879(5) 0.0858(15) Uani 1 1 d . . H3 H 0.965499 0.901588 0.115618 0.103 Uiso 1 1 calc R U C4 C 1.0093(7) 0.6266(8) 0.1511(5) 0.0843(15) Uani 1 1 d . . H4 H 1.096778 0.608677 0.055192 0.101 Uiso 1 1 calc R U C5 C 0.9590(5) 0.4771(7) 0.2552(4) 0.0709(12) Uani 1 1 d . . H5 H 1.010139 0.359043 0.229432 0.085 Uiso 1 1 calc R U C6 C 0.8296(5) 0.5049(5) 0.4006(4) 0.0516(9) Uani 1 1 d . . C7 C 0.7743(5) 0.3570(5) 0.5192(4) 0.0513(9) Uani 1 1 d . . H7 H 0.826775 0.235844 0.499775 0.062 Uiso 1 1 calc R U C8 C 0.6494(4) 0.3882(5) 0.6570(4) 0.0469(8) Uani 1 1 d . . C9 C 0.5675(5) 0.5799(5) 0.6859(4) 0.0500(9) Uani 1 1 d . . C10 C 0.6010(5) 0.2282(5) 0.7779(4) 0.0512(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 S1 0.0896(9) 0.0442(7) 0.0825(8) -0.0076(5) -0.0121(6) -0.0239(6) O1 0.0766(16) 0.0457(15) 0.0566(15) -0.0043(11) -0.0166(12) -0.0197(14) N1 0.088(2) 0.050(2) 0.059(2) -0.0150(14) -0.0070(17) -0.0144(18) N2 0.093(2) 0.056(2) 0.057(2) -0.0024(14) -0.0100(17) -0.0302(19) C1 0.0526(19) 0.055(2) 0.050(2) 0.0000(16) -0.0179(16) -0.0190(19) C2 0.080(3) 0.063(3) 0.070(3) 0.0097(19) -0.026(2) -0.029(2) C3 0.082(3) 0.083(4) 0.080(3) 0.025(3) -0.026(2) -0.036(3) C4 0.065(2) 0.112(4) 0.061(3) 0.006(3) -0.0111(19) -0.031(3) C5 0.058(2) 0.084(3) 0.060(2) -0.009(2) -0.0114(18) -0.015(2) C6 0.0419(17) 0.052(2) 0.056(2) -0.0045(16) -0.0162(14) -0.0097(17) C7 0.0484(18) 0.045(2) 0.060(2) -0.0128(15) -0.0165(16) -0.0091(16) C8 0.0453(18) 0.043(2) 0.054(2) -0.0100(14) -0.0152(15) -0.0125(16) C9 0.0547(19) 0.041(2) 0.054(2) -0.0055(15) -0.0179(16) -0.0128(17) C10 0.0562(18) 0.047(2) 0.053(2) -0.0028(15) -0.0163(15) -0.0215(17) 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 122.2(3) C6 C1 O1 120.5(3) C6 C1 C2 123.4(3) O1 C1 C2 116.0(3) C3 C2 C1 117.1(4) C4 C3 C2 121.4(4) C5 C4 C3 120.6(4) C4 C5 C6 119.3(4) C1 C6 C5 118.2(3) C1 C6 C7 118.2(3) C5 C6 C7 123.6(4) C8 C7 C6 122.2(3) C7 C8 C9 118.3(3) C7 C8 C10 120.0(3) C9 C8 C10 121.7(3) N1 C9 O1 117.0(3) N1 C9 C8 124.5(3) O1 C9 C8 118.5(3) N2 C10 C8 116.1(3) N2 C10 S1 121.9(3) C8 C10 S1 121.9(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance S1 C10 1.664(4) O1 C9 1.367(4) O1 C1 1.378(4) N1 C9 1.270(4) N2 C10 1.313(4) C1 C6 1.372(5) C1 C2 1.383(5) C2 C3 1.378(6) C3 C4 1.377(7) C4 C5 1.379(6) C5 C6 1.403(5) C6 C7 1.440(5) C7 C8 1.342(4) C8 C9 1.466(5) C8 C10 1.502(5) 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 1.93 2.643(4) 139.4 . N2 H2NB S1 0.86 2.67 3.506(3) 164.7 2_657 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 0.9(5) C9 O1 C1 C2 -177.5(3) C6 C1 C2 C3 2.4(6) O1 C1 C2 C3 -179.2(3) C1 C2 C3 C4 -1.6(6) C2 C3 C4 C5 1.0(7) C3 C4 C5 C6 -1.1(6) O1 C1 C6 C5 179.1(3) C2 C1 C6 C5 -2.5(5) O1 C1 C6 C7 -1.6(5) C2 C1 C6 C7 176.8(3) C4 C5 C6 C1 1.8(6) C4 C5 C6 C7 -177.5(4) C1 C6 C7 C8 1.1(5) C5 C6 C7 C8 -179.7(3) C6 C7 C8 C9 0.1(5) C6 C7 C8 C10 -178.4(3) C1 O1 C9 N1 179.4(3) C1 O1 C9 C8 0.3(5) C7 C8 C9 N1 -179.8(3) C10 C8 C9 N1 -1.3(5) C7 C8 C9 O1 -0.8(5) C10 C8 C9 O1 177.7(3) C7 C8 C10 N2 178.7(3) C9 C8 C10 N2 0.2(5) C7 C8 C10 S1 -0.9(5) C9 C8 C10 S1 -179.4(2)