#------------------------------------------------------------------------------ #$Date: 2018-03-20 05:44:44 +0200 (Tue, 20 Mar 2018) $ #$Revision: 207021 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/23/03/7230307.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_7230307 loop_ _publ_author_name 'Chopra, Deepak' 'Mondal, Pradip Kumar' 'Rao, Varun' _publ_section_title ; Capturing the metastable state in the spontaneous and reversible Single-Crystal-to-Single-Crystal phase transition in riluzolium oxalate ; _journal_name_full CrystEngComm _journal_paper_doi 10.1039/C8CE00283E _journal_year 2018 _chemical_formula_sum 'C9 H6 F3 N2 O3 S' _chemical_formula_weight 279.22 _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 mixed _audit_creation_method SHELXL-2016/6 _audit_update_record ; 2017-09-01 deposited with the CCDC. 2018-03-19 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 100.132(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 9.7557(4) _cell_length_b 10.0386(4) _cell_length_c 11.7809(4) _cell_measurement_reflns_used 2757 _cell_measurement_temperature 270(2) _cell_measurement_theta_max 26.77 _cell_measurement_theta_min 2.94 _cell_volume 1135.75(8) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2016/6 (Sheldrick, 2016)' _computing_structure_solution 'SHELXS-97 (Sheldrick 2008)' _diffrn_ambient_temperature 270(2) _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0315 _diffrn_reflns_av_unetI/netI 0.0358 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.994 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 11948 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.994 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 29.626 _diffrn_reflns_theta_min 2.121 _exptl_absorpt_coefficient_mu 0.328 _exptl_absorpt_correction_T_max 0.7510 _exptl_absorpt_correction_T_min 0.5086 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS 2014/4' _exptl_crystal_density_diffrn 1.633 _exptl_crystal_description Plate _exptl_crystal_F_000 564 _exptl_crystal_size_max 0.450 _exptl_crystal_size_mid 0.190 _exptl_crystal_size_min 0.050 _refine_diff_density_max 0.850 _refine_diff_density_min -0.446 _refine_diff_density_rms 0.077 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 175 _refine_ls_number_reflns 3175 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.049 _refine_ls_R_factor_all 0.1072 _refine_ls_R_factor_gt 0.0753 _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^)+(0.1326P)^2^+0.5926P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2202 _refine_ls_wR_factor_ref 0.2453 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2055 _reflns_number_total 3175 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c8ce00283e2.cif _cod_data_source_block RZ-OA-270K _cod_database_code 7230307 _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 0.867 _shelx_estimated_absorpt_t_max 0.984 _shelx_res_file ; TITL RA-OA-270K in P2(1)/c shelx.res created by SHELXL-2016/6 at 15:04:54 on 17-Aug-2017 CELL 0.71073 9.7557 10.0386 11.7809 90.000 100.132 90.000 ZERR 4.00 0.0004 0.0004 0.0004 0.000 0.003 0.000 LATT 1 SYMM -x, y+1/2, -z+1/2 SFAC C H N O F S UNIT 36 24 8 12 12 4 TEMP -3.0 ACTA L.S. 20 OMIT 0 2 0 OMIT -3 1 3 OMIT 0 4 3 FMAP 2 SIZE 0.45 0.19 0.05 PLAN 25 BOND $H CONF WGHT 0.132600 0.592600 FVAR 0.33187 S1 6 0.336484 0.581966 0.307927 11.00000 0.09081 0.04659 = 0.04376 0.01579 0.02620 0.02004 F1 5 -0.085883 0.717503 0.667461 11.00000 0.11640 0.38392 = 0.22560 -0.09057 0.08395 -0.06843 F2 5 -0.098097 0.791996 0.498524 11.00000 0.08304 0.19918 = 0.23810 -0.11620 -0.00729 0.02198 F3 5 -0.075722 0.930223 0.633913 11.00000 0.12348 0.20148 = 0.31744 -0.16487 0.07237 0.02677 O1 4 0.097164 0.804630 0.620044 11.00000 0.07539 0.12013 = 0.14513 -0.08289 0.03340 -0.00190 O2 4 0.480637 1.082448 0.368491 11.00000 0.14184 0.03932 = 0.02956 0.00582 0.03531 0.01352 O3 4 0.455197 1.158892 0.540800 11.00000 0.12190 0.03361 = 0.03196 0.00080 0.03105 0.01111 N1 3 0.450360 0.343616 0.280251 11.00000 0.09016 0.03974 = 0.03206 0.00477 0.02574 0.00832 H1B 2 0.476126 0.255337 0.303966 11.00000 0.06331 H1A 2 0.456124 0.373744 0.212743 11.00000 0.06169 N2 3 0.367464 0.386457 0.449867 11.00000 0.07295 0.03894 = 0.02909 0.00495 0.01858 0.00246 H2 2 0.393572 0.317324 0.487579 11.00000 0.06216 C1 1 0.391849 0.421603 0.345926 11.00000 0.06452 0.03688 = 0.02796 0.00412 0.01507 -0.00004 C2 1 0.296463 0.483234 0.501606 11.00000 0.06732 0.04693 = 0.03676 -0.00350 0.01968 -0.00274 C3 1 0.252507 0.473685 0.606769 11.00000 0.09902 0.06677 = 0.04603 -0.00591 0.03272 -0.00783 AFIX 43 H3 2 0.269143 0.397121 0.651518 11.00000 -1.20000 AFIX 0 C4 1 0.183189 0.581134 0.643421 11.00000 0.10110 0.09248 = 0.06196 -0.02702 0.04551 -0.01186 AFIX 43 H4 2 0.151965 0.577461 0.713532 11.00000 -1.20000 AFIX 0 C5 1 0.160687 0.692579 0.576505 11.00000 0.07096 0.07643 = 0.08427 -0.03599 0.03248 -0.00341 C6 1 0.202479 0.705063 0.472882 11.00000 0.07434 0.06090 = 0.07556 -0.00613 0.02590 0.01441 AFIX 43 H6 2 0.185861 0.782491 0.429288 11.00000 -1.20000 AFIX 0 C7 1 0.270614 0.597798 0.435288 11.00000 0.06359 0.04964 = 0.04866 -0.00036 0.01944 0.00533 C8 1 -0.032604 0.814508 0.600257 11.00000 0.07401 0.16623 = 0.20220 -0.11189 0.04274 -0.01868 C9 1 0.481840 1.069281 0.473267 11.00000 0.08251 0.03098 = 0.02968 -0.00062 0.02299 -0.00310 HKLF 4 REM RA-OA-270K in P2(1)/c REM R1 = 0.0753 for 2055 Fo > 4sig(Fo) and 0.1072 for all 3175 data REM 175 parameters refined using 0 restraints END WGHT 0.1326 0.5926 REM Highest difference peak 0.850, deepest hole -0.446, 1-sigma level 0.077 Q1 1 0.0893 0.9553 0.5377 11.00000 0.05 0.85 Q2 1 0.0216 0.7460 0.5957 11.00000 0.05 0.55 Q3 1 -0.0499 0.8786 0.4484 11.00000 0.05 0.51 Q4 1 0.2613 0.5355 0.2765 11.00000 0.05 0.46 Q5 1 -0.0729 0.9501 0.5962 11.00000 0.05 0.39 Q6 1 0.0825 0.6556 0.5474 11.00000 0.05 0.33 Q7 1 -0.0052 0.7964 0.7368 11.00000 0.05 0.29 Q8 1 0.1249 0.6663 0.4359 11.00000 0.05 0.28 Q9 1 -0.0585 0.8559 0.7077 11.00000 0.05 0.28 Q10 1 0.1128 0.5569 0.6081 11.00000 0.05 0.28 Q11 1 0.2993 0.5875 0.3603 11.00000 0.05 0.28 Q12 1 0.3872 0.4028 0.4013 11.00000 0.05 0.26 Q13 1 0.2137 0.5554 0.4086 11.00000 0.05 0.22 Q14 1 0.5186 1.1443 0.5470 11.00000 0.05 0.21 Q15 1 0.4400 1.1325 0.5032 11.00000 0.05 0.20 Q16 1 0.4672 1.0655 0.4123 11.00000 0.05 0.20 Q17 1 -0.0775 0.7469 0.5219 11.00000 0.05 0.20 Q18 1 0.5000 1.0000 0.5000 10.50000 0.05 0.20 Q19 1 0.2952 0.5478 0.4726 11.00000 0.05 0.19 Q20 1 0.5035 1.1655 0.5012 11.00000 0.05 0.18 Q21 1 0.3032 0.3552 0.4088 11.00000 0.05 0.18 Q22 1 0.1902 0.6325 0.6197 11.00000 0.05 0.18 Q23 1 0.3114 0.4391 0.6426 11.00000 0.05 0.18 Q24 1 0.2376 0.5354 0.6750 11.00000 0.05 0.18 Q25 1 0.4383 0.2960 0.2845 11.00000 0.05 0.17 ; _shelx_res_checksum 7788 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 S1 S 0.33648(10) 0.58197(8) 0.30793(7) 0.0586(3) Uani 1 1 d . . F1 F -0.0859(5) 0.7175(9) 0.6675(6) 0.235(4) Uani 1 1 d . . F2 F -0.0981(4) 0.7920(5) 0.4985(5) 0.178(2) Uani 1 1 d . . F3 F -0.0757(4) 0.9302(6) 0.6339(6) 0.210(3) Uani 1 1 d . . O1 O 0.0972(3) 0.8046(4) 0.6200(4) 0.1119(14) Uani 1 1 d . . O2 O 0.4806(3) 1.0824(2) 0.36849(17) 0.0678(8) Uani 1 1 d . . O3 O 0.4552(3) 1.1589(2) 0.54080(16) 0.0604(7) Uani 1 1 d . . N1 N 0.4504(3) 0.3436(3) 0.2803(2) 0.0522(7) Uani 1 1 d . . H1B H 0.476(4) 0.255(4) 0.304(3) 0.063(10) Uiso 1 1 d . . H1A H 0.456(4) 0.374(4) 0.213(4) 0.062(10) Uiso 1 1 d . . N2 N 0.3675(3) 0.3865(3) 0.44987(19) 0.0458(6) Uani 1 1 d . . H2 H 0.394(4) 0.317(4) 0.488(3) 0.062(10) Uiso 1 1 d . . C1 C 0.3918(3) 0.4216(3) 0.3459(2) 0.0423(6) Uani 1 1 d . . C2 C 0.2965(3) 0.4832(3) 0.5016(2) 0.0491(7) Uani 1 1 d . . C3 C 0.2525(4) 0.4737(4) 0.6068(3) 0.0682(10) Uani 1 1 d . . H3 H 0.269143 0.397121 0.651518 0.082 Uiso 1 1 calc R U C4 C 0.1832(5) 0.5811(5) 0.6434(4) 0.0814(13) Uani 1 1 d . . H4 H 0.151965 0.577461 0.713532 0.098 Uiso 1 1 calc R U C5 C 0.1607(4) 0.6926(5) 0.5765(4) 0.0749(12) Uani 1 1 d . . C6 C 0.2025(4) 0.7051(4) 0.4729(4) 0.0687(10) Uani 1 1 d . . H6 H 0.185861 0.782491 0.429288 0.082 Uiso 1 1 calc R U C7 C 0.2706(3) 0.5978(3) 0.4353(3) 0.0528(7) Uani 1 1 d . . C8 C -0.0326(6) 0.8145(9) 0.6003(9) 0.145(3) Uani 1 1 d . . C9 C 0.4818(3) 1.0693(3) 0.4733(2) 0.0461(7) 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 0.0908(7) 0.0466(5) 0.0438(4) 0.0158(3) 0.0262(4) 0.0200(4) F1 0.116(3) 0.384(11) 0.226(6) -0.091(6) 0.084(4) -0.068(5) F2 0.083(2) 0.199(4) 0.238(5) -0.116(4) -0.007(3) 0.022(2) F3 0.123(3) 0.201(5) 0.317(7) -0.165(5) 0.072(4) 0.027(3) O1 0.075(2) 0.120(3) 0.145(3) -0.083(3) 0.0334(19) -0.0019(18) O2 0.142(2) 0.0393(12) 0.0296(10) 0.0058(8) 0.0353(12) 0.0135(13) O3 0.122(2) 0.0336(11) 0.0320(9) 0.0008(7) 0.0311(11) 0.0111(11) N1 0.090(2) 0.0397(14) 0.0321(11) 0.0048(9) 0.0257(12) 0.0083(13) N2 0.0729(16) 0.0389(13) 0.0291(10) 0.0050(9) 0.0186(10) 0.0025(11) C1 0.0645(16) 0.0369(14) 0.0280(11) 0.0041(9) 0.0151(11) 0.0000(12) C2 0.0673(18) 0.0469(17) 0.0368(13) -0.0035(11) 0.0197(12) -0.0027(14) C3 0.099(3) 0.067(2) 0.0460(17) -0.0059(15) 0.0327(17) -0.008(2) C4 0.101(3) 0.092(3) 0.062(2) -0.027(2) 0.046(2) -0.012(2) C5 0.071(2) 0.076(3) 0.084(3) -0.036(2) 0.032(2) -0.003(2) C6 0.074(2) 0.061(2) 0.076(2) -0.0061(18) 0.0259(18) 0.0144(18) C7 0.0636(18) 0.0496(18) 0.0487(16) -0.0004(12) 0.0194(13) 0.0053(14) C8 0.074(3) 0.166(7) 0.202(8) -0.112(6) 0.043(4) -0.019(4) C9 0.083(2) 0.0310(14) 0.0297(12) -0.0006(9) 0.0230(12) -0.0031(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' F F 0.0171 0.0103 '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 _geom_angle_site_symmetry_3 C1 S1 C7 90.44(14) . C8 O1 C5 119.1(4) . C1 N1 H1B 121(2) . C1 N1 H1A 116(3) . H1B N1 H1A 123(4) . C1 N2 C2 113.5(2) . C1 N2 H2 128(3) . C2 N2 H2 118(3) . N1 C1 N2 123.6(3) . N1 C1 S1 123.7(2) . N2 C1 S1 112.6(2) . C3 C2 C7 120.5(3) . C3 C2 N2 126.8(3) . C7 C2 N2 112.7(3) . C4 C3 C2 118.1(4) . C4 C3 H3 120.9 . C2 C3 H3 120.9 . C5 C4 C3 119.8(4) . C5 C4 H4 120.1 . C3 C4 H4 120.1 . C6 C5 C4 123.5(4) . C6 C5 O1 118.0(5) . C4 C5 O1 118.4(4) . C5 C6 C7 117.0(4) . C5 C6 H6 121.5 . C7 C6 H6 121.5 . C6 C7 C2 121.1(3) . C6 C7 S1 128.3(3) . C2 C7 S1 110.6(2) . O1 C8 F2 119.0(6) . O1 C8 F3 112.3(5) . F2 C8 F3 107.7(8) . O1 C8 F1 107.6(8) . F2 C8 F1 103.4(6) . F3 C8 F1 105.7(7) . O2 C9 O3 125.9(3) . O2 C9 C9 117.7(3) 3_676 O3 C9 C9 116.4(3) 3_676 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 S1 C1 1.732(3) . S1 C7 1.740(3) . F1 C8 1.411(12) . F2 C8 1.275(9) . F3 C8 1.320(7) . O1 C8 1.250(7) . O1 C5 1.423(5) . O2 C9 1.239(3) . O3 C9 1.258(3) . N1 C1 1.301(4) . N1 H1B 0.95(4) . N1 H1A 0.86(4) . N2 C1 1.335(3) . N2 C2 1.394(4) . N2 H2 0.84(4) . C2 C3 1.384(4) . C2 C7 1.388(4) . C3 C4 1.382(6) . C3 H3 0.9300 . C4 C5 1.364(7) . C4 H4 0.9300 . C5 C6 1.359(6) . C6 C7 1.379(5) . C6 H6 0.9300 . C9 C9 1.542(5) 3_676 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 C2 N2 C1 N1 -176.4(3) C2 N2 C1 S1 3.3(3) C7 S1 C1 N1 177.0(3) C7 S1 C1 N2 -2.8(2) C1 N2 C2 C3 177.6(3) C1 N2 C2 C7 -2.1(4) C7 C2 C3 C4 -0.2(6) N2 C2 C3 C4 -180.0(4) C2 C3 C4 C5 -0.3(6) C3 C4 C5 C6 0.4(7) C3 C4 C5 O1 -176.0(4) C8 O1 C5 C6 93.8(8) C8 O1 C5 C4 -89.7(8) C4 C5 C6 C7 0.2(6) O1 C5 C6 C7 176.5(3) C5 C6 C7 C2 -0.8(6) C5 C6 C7 S1 179.9(3) C3 C2 C7 C6 0.8(5) N2 C2 C7 C6 -179.4(3) C3 C2 C7 S1 -179.8(3) N2 C2 C7 S1 0.0(4) C1 S1 C7 C6 -179.1(4) C1 S1 C7 C2 1.5(3) C5 O1 C8 F2 -45.4(12) C5 O1 C8 F3 -172.5(7) C5 O1 C8 F1 71.6(8)