#------------------------------------------------------------------------------ #$Date: 2021-07-22 07:27:59 +0300 (Thu, 22 Jul 2021) $ #$Revision: 267691 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/81/7158184.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_7158184 loop_ _publ_author_name 'Patel, Bhisma K.' 'Chakraborty, Nikita' 'Dahiya, Anjali' 'Rakshit, Amitava' 'Modi, Anju' _publ_section_title ; An expedient route to tricyanovinylindoles and indolylmaleimides from o-alkynylanilines utilising DMSO as one-carbon synthon ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/D1OB01086G _journal_year 2021 _chemical_compound_source NA _chemical_formula_sum 'C20 H11 F N4' _chemical_formula_weight 326.33 _chemical_name_systematic 2-(5-fluoro-2-(p-tolyl)-1H-indol-3-yl)ethene-1,1,2-tricarbonitrile _chemical_properties_physical Heat-sensitive _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' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2020-12-19 deposited with the CCDC. 2021-07-20 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 94.167(6) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 11.4106(7) _cell_length_b 14.3958(14) _cell_length_c 9.9664(5) _cell_measurement_reflns_used 1572 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 27.4520 _cell_measurement_theta_min 2.8230 _cell_volume 1632.8(2) _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 293(2) _diffrn_detector 'CCD plate' _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.874 _diffrn_measurement_device_type 'SuperNova, Single source at offset/far, Eos' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0343 _diffrn_reflns_av_unetI/netI 0.0789 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.874 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 7751 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.874 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.743 _diffrn_reflns_theta_min 2.281 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details SADABS _exptl_crystal_colour red _exptl_crystal_density_diffrn 1.327 _exptl_crystal_description cube _exptl_crystal_F_000 672 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: Dichloromethane' _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.22 _exptl_transmission_factor_max 0.980 _exptl_transmission_factor_min 0.977 _refine_diff_density_max 0.168 _refine_diff_density_min -0.176 _refine_diff_density_rms 0.039 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.952 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 227 _refine_ls_number_reflns 3709 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.952 _refine_ls_R_factor_all 0.1181 _refine_ls_R_factor_gt 0.0521 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0488P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1099 _refine_ls_wR_factor_ref 0.1383 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1842 _reflns_number_total 3709 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1ob01086g2.cif _cod_data_source_block exp_6155 _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 7158184 _shelx_shelxl_version_number 2018/3 _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_res_file ; TITL exp_6155_a.res in P2(1)/c exp_6155.res created by SHELXL-2018/3 at 21:04:25 on 21-Feb-2019 REM Old TITL exp_6155 in P2(1)/c REM SHELXT solution in P2(1)/c: R1 0.187, Rweak 0.409, Alpha 0.031 REM 0.593 for 144 systematic absences, Orientation as input REM Formula found by SHELXT: C20 N4 F CELL 0.71073 11.4106 14.3958 9.9664 90 94.167 90 ZERR 4 0.0007 0.0014 0.0005 0 0.006 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H F N UNIT 80 44 4 16 L.S. 4 PLAN -1 BOND LIST 6 fmap 2 ACTA REM REM REM WGHT 0.048800 FVAR 0.81731 F17 3 -0.074155 0.712897 0.786403 11.00000 0.08239 0.05308 = 0.08749 -0.00782 -0.00990 0.01848 N9 4 0.242231 0.483579 1.048128 11.00000 0.06292 0.05368 = 0.02387 0.00040 0.00116 -0.00349 AFIX 43 H9 2 0.263325 0.475799 1.131977 11.00000 -1.20000 AFIX 0 N21 4 -0.030392 0.405153 0.595464 11.00000 0.05827 0.06324 = 0.04935 0.00323 -0.00151 -0.00330 N23 4 0.257393 0.431695 0.339377 11.00000 0.06510 0.07789 = 0.03327 -0.00452 0.00051 0.00270 C3 1 0.145038 0.535460 0.858659 11.00000 0.04700 0.03872 = 0.03087 -0.00023 0.00265 -0.00723 C2 1 0.231222 0.468211 0.824863 11.00000 0.04986 0.04031 = 0.02765 0.00134 0.00026 -0.00342 C18 1 0.265579 0.446236 0.692053 11.00000 0.04816 0.03745 = 0.03075 0.00199 0.00224 -0.00079 C1 1 0.289743 0.438185 0.946425 11.00000 0.05429 0.04399 = 0.02830 -0.00175 0.00270 -0.00720 C19 1 0.190063 0.434591 0.581200 11.00000 0.05021 0.03831 = 0.02967 0.00151 0.00107 -0.00201 C8 1 0.155350 0.544082 0.999497 11.00000 0.05123 0.04375 = 0.03425 -0.00163 0.00665 -0.00446 C20 1 0.067465 0.419712 0.591657 11.00000 0.05588 0.03883 = 0.03192 -0.00146 -0.00012 0.00246 C10 1 0.385481 0.371409 0.968948 11.00000 0.05086 0.04236 = 0.03455 0.00499 0.00050 -0.00375 C22 1 0.229448 0.431998 0.447459 11.00000 0.05550 0.04686 = 0.03267 -0.00146 -0.00363 -0.00082 C4 1 0.066613 0.595133 0.785156 11.00000 0.06190 0.03890 = 0.04029 -0.00270 -0.00178 -0.00352 AFIX 43 H4 2 0.058406 0.593564 0.691659 11.00000 -1.20000 AFIX 0 C24 1 0.389889 0.444958 0.672321 11.00000 0.05826 0.05654 = 0.03215 -0.00549 0.00304 -0.00419 N25 4 0.488247 0.448321 0.658870 11.00000 0.06210 0.10069 = 0.06772 -0.01058 0.01349 -0.00800 C5 1 0.003292 0.655216 0.856535 11.00000 0.05848 0.03899 = 0.06164 -0.00196 -0.00496 0.00096 C7 1 0.089541 0.605807 1.069098 11.00000 0.07149 0.05143 = 0.03939 -0.00645 0.01701 -0.00723 AFIX 43 H7 2 0.097680 0.609110 1.162502 11.00000 -1.20000 AFIX 0 C11 1 0.478013 0.390265 1.063564 11.00000 0.06487 0.05109 = 0.04274 0.00099 -0.00643 -0.00887 AFIX 43 H11 2 0.475865 0.442796 1.117646 11.00000 -1.20000 AFIX 0 C15 1 0.389303 0.290280 0.894111 11.00000 0.06595 0.05059 = 0.04716 -0.00265 -0.00264 -0.00340 AFIX 43 H15 2 0.326977 0.275401 0.832531 11.00000 -1.20000 AFIX 0 C6 1 0.011784 0.662054 0.995729 11.00000 0.06548 0.04538 = 0.06074 -0.01245 0.01886 -0.00199 AFIX 43 H6 2 -0.034595 0.704191 1.038756 11.00000 -1.20000 AFIX 0 C12 1 0.572961 0.330911 1.077031 11.00000 0.05641 0.06192 = 0.07076 0.01402 -0.01457 -0.00587 AFIX 43 H12 2 0.634482 0.344520 1.140339 11.00000 -1.20000 AFIX 0 C13 1 0.579563 0.251508 0.999052 11.00000 0.05695 0.05058 = 0.07972 0.01529 0.00850 0.00201 C14 1 0.484454 0.231770 0.910291 11.00000 0.06970 0.04931 = 0.07017 -0.00219 0.00509 0.00293 AFIX 43 H14 2 0.484704 0.177366 0.859992 11.00000 -1.20000 AFIX 0 C16 1 0.685608 0.189211 1.013862 11.00000 0.06521 0.08061 = 0.14521 0.01907 0.01224 0.01242 AFIX 137 H16A 2 0.754385 0.225884 1.037034 11.00000 -1.50000 H16B 2 0.694527 0.157526 0.930462 11.00000 -1.50000 H16C 2 0.675565 0.144479 1.083539 11.00000 -1.50000 AFIX 0 HKLF 4 REM exp_6155_a.res in P2(1)/c REM wR2 = 0.1383, GooF = S = 0.952, Restrained GooF = 0.952 for all data REM R1 = 0.0521 for 1842 Fo > 4sig(Fo) and 0.1181 for all 3709 data REM 227 parameters refined using 0 restraints END WGHT 0.0488 0.0000 REM Highest difference peak 0.168, deepest hole -0.176, 1-sigma level 0.039 Q1 1 0.1600 0.5538 0.9192 11.00000 0.05 0.17 ; _shelx_res_checksum 54422 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 _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group F17 F -0.07415(13) 0.71290(11) 0.78640(15) 0.0751(5) Uani 1 1 d . . . . . N9 N 0.24223(16) 0.48358(14) 1.04813(15) 0.0469(5) Uani 1 1 d . . . . . H9 H 0.263325 0.475799 1.131977 0.056 Uiso 1 1 calc R U . . . N21 N -0.03039(19) 0.40515(16) 0.59546(18) 0.0572(6) Uani 1 1 d . . . . . N23 N 0.25739(17) 0.43169(17) 0.33938(17) 0.0589(6) Uani 1 1 d . . . . . C3 C 0.14504(18) 0.53546(16) 0.85866(19) 0.0389(6) Uani 1 1 d . . . . . C2 C 0.23122(19) 0.46821(17) 0.82486(18) 0.0394(6) Uani 1 1 d . . . . . C18 C 0.26558(18) 0.44624(16) 0.69205(18) 0.0388(6) Uani 1 1 d . . . . . C1 C 0.2897(2) 0.43818(17) 0.94643(19) 0.0422(6) Uani 1 1 d . . . . . C19 C 0.19006(19) 0.43459(16) 0.58120(18) 0.0395(6) Uani 1 1 d . . . . . C8 C 0.15535(19) 0.54408(17) 0.99950(19) 0.0429(6) Uani 1 1 d . . . . . C20 C 0.0675(2) 0.41971(17) 0.59166(19) 0.0424(6) Uani 1 1 d . . . . . C10 C 0.38548(19) 0.37141(18) 0.96895(19) 0.0427(6) Uani 1 1 d . . . . . C22 C 0.22945(19) 0.43200(18) 0.4475(2) 0.0453(6) Uani 1 1 d . . . . . C4 C 0.0666(2) 0.59513(17) 0.7852(2) 0.0473(6) Uani 1 1 d . . . . . H4 H 0.058406 0.593564 0.691659 0.057 Uiso 1 1 calc R U . . . C24 C 0.3899(2) 0.44496(19) 0.67232(19) 0.0490(7) Uani 1 1 d . . . . . N25 N 0.4882(2) 0.4483(2) 0.6589(2) 0.0764(8) Uani 1 1 d . . . . . C5 C 0.0033(2) 0.65522(19) 0.8565(2) 0.0535(7) Uani 1 1 d . . . . . C7 C 0.0895(2) 0.60581(19) 1.0691(2) 0.0535(7) Uani 1 1 d . . . . . H7 H 0.097680 0.609110 1.162502 0.064 Uiso 1 1 calc R U . . . C11 C 0.4780(2) 0.39027(19) 1.0636(2) 0.0534(7) Uani 1 1 d . . . . . H11 H 0.475865 0.442796 1.117646 0.064 Uiso 1 1 calc R U . . . C15 C 0.3893(2) 0.29028(19) 0.8941(2) 0.0549(7) Uani 1 1 d . . . . . H15 H 0.326977 0.275401 0.832531 0.066 Uiso 1 1 calc R U . . . C6 C 0.0118(2) 0.66205(19) 0.9957(2) 0.0565(7) Uani 1 1 d . . . . . H6 H -0.034595 0.704191 1.038756 0.068 Uiso 1 1 calc R U . . . C12 C 0.5730(2) 0.3309(2) 1.0770(3) 0.0640(8) Uani 1 1 d . . . . . H12 H 0.634482 0.344520 1.140339 0.077 Uiso 1 1 calc R U . . . C13 C 0.5796(2) 0.2515(2) 0.9991(3) 0.0622(8) Uani 1 1 d . . . . . C14 C 0.4845(2) 0.2318(2) 0.9103(2) 0.0631(8) Uani 1 1 d . . . . . H14 H 0.484704 0.177366 0.859992 0.076 Uiso 1 1 calc R U . . . C16 C 0.6856(2) 0.1892(2) 1.0139(3) 0.0968(11) Uani 1 1 d . . . . . H16A H 0.754385 0.225884 1.037034 0.145 Uiso 1 1 calc R U . . . H16B H 0.694527 0.157526 0.930462 0.145 Uiso 1 1 calc R U . . . H16C H 0.675565 0.144479 1.083539 0.145 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 F17 0.0824(11) 0.0531(11) 0.0875(11) -0.0078(8) -0.0099(9) 0.0185(9) N9 0.0629(12) 0.0537(15) 0.0239(8) 0.0004(9) 0.0012(8) -0.0035(12) N21 0.0583(13) 0.0632(18) 0.0493(12) 0.0032(11) -0.0015(10) -0.0033(14) N23 0.0651(14) 0.0779(18) 0.0333(10) -0.0045(10) 0.0005(9) 0.0027(13) C3 0.0470(13) 0.0387(15) 0.0309(10) -0.0002(10) 0.0027(9) -0.0072(13) C2 0.0499(13) 0.0403(15) 0.0277(10) 0.0013(10) 0.0003(9) -0.0034(13) C18 0.0482(13) 0.0375(15) 0.0307(10) 0.0020(9) 0.0022(9) -0.0008(12) C1 0.0543(14) 0.0440(16) 0.0283(10) -0.0018(10) 0.0027(9) -0.0072(13) C19 0.0502(13) 0.0383(15) 0.0297(10) 0.0015(10) 0.0011(9) -0.0020(13) C8 0.0512(13) 0.0438(16) 0.0343(11) -0.0016(11) 0.0066(10) -0.0045(13) C20 0.0559(15) 0.0388(16) 0.0319(10) -0.0015(10) -0.0001(10) 0.0025(14) C10 0.0509(14) 0.0424(16) 0.0345(11) 0.0050(11) 0.0005(10) -0.0037(13) C22 0.0555(15) 0.0469(17) 0.0327(11) -0.0015(11) -0.0036(10) -0.0008(13) C4 0.0619(16) 0.0389(16) 0.0403(12) -0.0027(11) -0.0018(11) -0.0035(14) C24 0.0583(16) 0.0565(19) 0.0321(11) -0.0055(11) 0.0030(11) -0.0042(16) N25 0.0621(14) 0.101(2) 0.0677(14) -0.0106(13) 0.0135(12) -0.0080(16) C5 0.0585(16) 0.0390(17) 0.0616(15) -0.0020(13) -0.0050(13) 0.0010(14) C7 0.0715(17) 0.0514(18) 0.0394(12) -0.0065(12) 0.0170(12) -0.0072(16) C11 0.0649(16) 0.0511(18) 0.0427(13) 0.0010(12) -0.0064(12) -0.0089(15) C15 0.0660(17) 0.0506(19) 0.0472(13) -0.0026(12) -0.0026(12) -0.0034(16) C6 0.0655(16) 0.0454(18) 0.0607(15) -0.0124(13) 0.0189(13) -0.0020(15) C12 0.0564(16) 0.062(2) 0.0708(17) 0.0140(16) -0.0146(14) -0.0059(17) C13 0.0570(16) 0.051(2) 0.0797(18) 0.0153(15) 0.0085(14) 0.0020(16) C14 0.0697(18) 0.049(2) 0.0702(17) -0.0022(14) 0.0051(14) 0.0029(16) C16 0.0652(19) 0.081(3) 0.145(3) 0.019(2) 0.0122(19) 0.012(2) 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' F F 0.0171 0.0103 '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' 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_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N9 C8 111.01(17) . . ? C8 C3 C4 118.0(2) . . ? C8 C3 C2 106.53(18) . . ? C4 C3 C2 135.17(19) . . ? C1 C2 C3 107.15(18) . . ? C1 C2 C18 125.4(2) . . ? C3 C2 C18 126.79(18) . . ? C19 C18 C2 125.0(2) . . ? C19 C18 C24 117.22(18) . . ? C2 C18 C24 117.53(17) . . ? N9 C1 C2 107.8(2) . . ? N9 C1 C10 122.63(18) . . ? C2 C1 C10 129.6(2) . . ? C18 C19 C20 121.70(19) . . ? C18 C19 C22 122.2(2) . . ? C20 C19 C22 115.98(17) . . ? N9 C8 C7 129.2(2) . . ? N9 C8 C3 107.5(2) . . ? C7 C8 C3 123.3(2) . . ? N21 C20 C19 177.0(3) . . ? C15 C10 C11 118.5(2) . . ? C15 C10 C1 121.6(2) . . ? C11 C10 C1 119.9(2) . . ? N23 C22 C19 177.6(3) . . ? C5 C4 C3 117.2(2) . . ? N25 C24 C18 176.7(3) . . ? C4 C5 F17 117.8(2) . . ? C4 C5 C6 124.5(2) . . ? F17 C5 C6 117.6(2) . . ? C6 C7 C8 117.8(2) . . ? C12 C11 C10 119.8(3) . . ? C14 C15 C10 120.5(2) . . ? C7 C6 C5 119.1(2) . . ? C11 C12 C13 122.0(2) . . ? C14 C13 C12 117.2(3) . . ? C14 C13 C16 122.0(3) . . ? C12 C13 C16 120.8(3) . . ? C15 C14 C13 121.8(3) . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F17 C5 1.367(3) . ? N9 C1 1.352(3) . ? N9 C8 1.381(3) . ? N21 C20 1.139(3) . ? N23 C22 1.145(3) . ? C3 C8 1.406(3) . ? C3 C4 1.407(3) . ? C3 C2 1.437(3) . ? C2 C1 1.408(3) . ? C2 C18 1.443(3) . ? C18 C19 1.361(3) . ? C18 C24 1.446(3) . ? C1 C10 1.460(3) . ? C19 C20 1.426(3) . ? C19 C22 1.438(3) . ? C8 C7 1.382(3) . ? C10 C15 1.388(3) . ? C10 C11 1.390(3) . ? C4 C5 1.360(3) . ? C24 N25 1.141(3) . ? C5 C6 1.387(3) . ? C7 C6 1.372(3) . ? C11 C12 1.379(4) . ? C15 C14 1.374(3) . ? C12 C13 1.387(4) . ? C13 C14 1.379(3) . ? C13 C16 1.505(4) . ?