#------------------------------------------------------------------------------ #$Date: 2020-02-04 22:09:27 +0200 (Tue, 04 Feb 2020) $ #$Revision: 247616 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/56/7125673.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_7125673 loop_ _publ_author_name 'Biswas, Aniruddha' 'Bera, Satabdi' 'Poddar, Puja' 'Dhara, Dibakar' 'Samanta, Rajarshi' _publ_section_title ; Rh(iii)-Catalyzed tandem indole C4-arylamination/annulation with anthranils: access to indoloquinolines and their application in photophysical studies. ; _journal_issue 9 _journal_name_full 'Chemical communications (Cambridge, England)' _journal_page_first 1440 _journal_page_last 1443 _journal_paper_doi 10.1039/c9cc08372c _journal_volume 56 _journal_year 2020 _chemical_formula_sum 'C23 H15 N3' _chemical_formula_weight 333.38 _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' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2019-07-30 deposited with the CCDC. 2019-12-19 downloaded from the CCDC. ; _cell_angle_alpha 90.00 _cell_angle_beta 111.20(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 9.549(2) _cell_length_b 21.299(4) _cell_length_c 9.583(2) _cell_measurement_reflns_used 2581 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 23.259 _cell_measurement_theta_min 1.912 _cell_volume 1817.1(7) _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.993 _diffrn_measurement_device_type 'Bruker SMART APEX' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0917 _diffrn_reflns_av_unetI/netI 0.0562 _diffrn_reflns_Laue_measured_fraction_full 0.993 _diffrn_reflns_Laue_measured_fraction_max 0.993 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 17692 _diffrn_reflns_point_group_measured_fraction_full 0.993 _diffrn_reflns_point_group_measured_fraction_max 0.993 _diffrn_reflns_theta_full 23.259 _diffrn_reflns_theta_max 23.259 _diffrn_reflns_theta_min 1.912 _exptl_absorpt_coefficient_mu 0.073 _exptl_absorpt_correction_T_max 0.7954 _exptl_absorpt_correction_T_min 0.6319 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details SADABS _exptl_crystal_colour Yellow _exptl_crystal_density_diffrn 1.219 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Needle _exptl_crystal_F_000 696 _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.07 _refine_diff_density_max 0.145 _refine_diff_density_min -0.159 _refine_diff_density_rms 0.035 _refine_ls_extinction_coef 0.016(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2014/7 (Sheldrick 2014' _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 236 _refine_ls_number_reflns 2581 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.031 _refine_ls_R_factor_all 0.0897 _refine_ls_R_factor_gt 0.0495 _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^)+(0.0717P)^2^+0.1023P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1274 _refine_ls_wR_factor_ref 0.1548 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1506 _reflns_number_total 2581 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9cc08372c2.cif _cod_data_source_block A _cod_depositor_comments 'Adding full bibliography for 7125673.cif.' _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 7125673 _shelx_shelxl_version_number 2014/7 _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 ; shelx.res created by SHELXL-2014/7 TITL rs_ab_2010_a.res in P2(1)/n CELL 0.71073 9.5487 21.2987 9.5833 90.000 111.203 90.000 ZERR 4.00 0.0020 0.0040 0.0020 0.030 0.030 0.030 LATT 1 SYMM 1/2 - X, 1/2 + Y, 1/2 - Z SFAC C H N UNIT 92 60 12 MERG 2 FMAP 2 PLAN 2 ACTA BOND $H LIST 6 L.S. 10 WGHT 0.071700 0.102300 EXTI 0.016378 FVAR 0.64082 N2 3 0.832336 0.461203 0.654890 11.00000 0.07062 0.05419 = 0.06774 -0.00138 0.02603 0.00140 N3 3 0.385101 0.367309 0.322667 11.00000 0.06835 0.07399 = 0.09604 -0.01706 0.02410 -0.00293 C9 1 0.937279 0.509140 0.692388 11.00000 0.06743 0.05526 = 0.06499 -0.00383 0.02742 0.00361 C3 1 0.602518 0.415392 0.475130 11.00000 0.06584 0.05548 = 0.07439 -0.00347 0.02493 0.00669 C10 1 0.933640 0.560996 0.592989 11.00000 0.07402 0.05603 = 0.07299 -0.00301 0.03130 0.00074 C8 1 0.718339 0.464253 0.519211 11.00000 0.06784 0.05348 = 0.06649 -0.00343 0.02346 0.00610 C7 1 0.702968 0.514907 0.410624 11.00000 0.07815 0.05678 = 0.06897 0.00040 0.02312 0.00563 N1 3 0.730054 0.308559 0.808367 11.00000 0.09100 0.09553 = 0.11969 0.02797 0.03122 0.00148 C4 1 0.481621 0.419296 0.336120 11.00000 0.06935 0.06657 = 0.08125 -0.00814 0.02173 0.00831 C2 1 0.576854 0.358213 0.547551 11.00000 0.06756 0.06234 = 0.08449 -0.00452 0.02656 0.00348 C15 1 1.054544 0.508401 0.838476 11.00000 0.08257 0.06569 = 0.07185 -0.00203 0.02185 -0.00055 AFIX 43 H15 2 1.060933 0.474815 0.902506 11.00000 -1.20000 AFIX 0 C17 1 0.256369 0.332526 0.052386 11.00000 0.07096 0.06248 = 0.09125 -0.00972 0.02758 -0.00403 C11 1 0.814203 0.562011 0.451851 11.00000 0.08647 0.05830 = 0.07381 0.00612 0.03169 0.00668 AFIX 43 H11 2 0.809229 0.594423 0.385196 11.00000 -1.20000 AFIX 0 C1 1 0.665082 0.332165 0.692242 11.00000 0.07218 0.06329 = 0.10669 0.00164 0.03895 -0.00450 C23 1 0.443720 0.331129 0.449360 11.00000 0.07758 0.06829 = 0.10119 -0.00648 0.03627 0.00004 AFIX 43 H23 2 0.401355 0.294128 0.467355 11.00000 -1.20000 AFIX 0 C6 1 0.574953 0.515429 0.267865 11.00000 0.09841 0.07089 = 0.07270 0.00702 0.01986 0.01521 AFIX 43 H6 2 0.566825 0.548019 0.200793 11.00000 -1.20000 AFIX 0 C12 1 1.047316 0.609591 0.644119 11.00000 0.08703 0.06339 = 0.09234 0.00137 0.03635 -0.00273 AFIX 43 H12 2 1.046998 0.642424 0.580031 11.00000 -1.20000 AFIX 0 C5 1 0.466225 0.469190 0.229793 11.00000 0.08034 0.07920 = 0.08270 -0.00621 0.00800 0.00941 AFIX 43 H5 2 0.385919 0.470181 0.138825 11.00000 -1.20000 AFIX 0 C14 1 1.157751 0.556837 0.885007 11.00000 0.08001 0.07923 = 0.08487 -0.00763 0.01137 -0.00295 AFIX 43 H14 2 1.229421 0.556451 0.981433 11.00000 -1.20000 AFIX 0 C22 1 0.392708 0.316656 0.037893 11.00000 0.08976 0.08428 = 0.11631 -0.01611 0.04462 0.00024 AFIX 43 H22 2 0.482249 0.321433 0.119009 11.00000 -1.20000 AFIX 0 C13 1 1.155057 0.608074 0.784851 11.00000 0.08013 0.07067 = 0.10900 -0.01069 0.02815 -0.01212 AFIX 43 H13 2 1.226349 0.639895 0.816019 11.00000 -1.20000 AFIX 0 C18 1 0.122644 0.325882 -0.073535 11.00000 0.09626 0.07655 = 0.09112 -0.00167 0.02729 -0.00745 AFIX 43 H18 2 0.031423 0.336976 -0.066048 11.00000 -1.20000 AFIX 0 C16 1 0.241275 0.355645 0.197517 11.00000 0.06053 0.10165 = 0.10395 -0.02808 0.02092 0.00081 AFIX 23 H16A 2 0.183531 0.394266 0.176456 11.00000 -1.20000 H16B 2 0.184601 0.324761 0.229647 11.00000 -1.20000 AFIX 0 C21 1 0.394968 0.293348 -0.099764 11.00000 0.14902 0.08257 = 0.14888 0.00920 0.09509 0.01637 AFIX 43 H21 2 0.485749 0.282803 -0.108962 11.00000 -1.20000 AFIX 0 C20 1 0.259538 0.286205 -0.222440 11.00000 0.21241 0.07881 = 0.09704 0.01087 0.08241 0.00490 AFIX 43 H20 2 0.260339 0.270249 -0.312482 11.00000 -1.20000 AFIX 0 C19 1 0.124981 0.303003 -0.208754 11.00000 0.16001 0.09521 = 0.08936 0.00407 0.03637 -0.00806 AFIX 43 H19 2 0.035615 0.298974 -0.290413 11.00000 -1.20000 AFIX 0 HKLF 4 REM rs_ab_2010_a.res in P2(1)/n REM R1 = 0.0495 for 1506 Fo > 4sig(Fo) and 0.0897 for all 2581 data REM 236 parameters refined using 0 restraints END WGHT 0.0716 0.1019 REM Highest difference peak 0.145, deepest hole -0.159, 1-sigma level 0.035 Q1 1 0.7551 0.4674 0.4484 11.00000 0.05 0.15 Q2 1 0.9629 0.6658 0.5185 11.00000 0.05 0.14 ; _shelx_res_checksum 7864 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 N2 N 0.8323(2) 0.46120(8) 0.6549(2) 0.0639(6) Uani 1 1 d . . N3 N 0.3851(2) 0.36731(11) 0.3227(3) 0.0810(7) Uani 1 1 d . . C9 C 0.9373(3) 0.50914(11) 0.6924(3) 0.0616(7) Uani 1 1 d . . C3 C 0.6025(3) 0.41539(11) 0.4751(3) 0.0654(7) Uani 1 1 d . . C10 C 0.9336(3) 0.56100(11) 0.5930(3) 0.0664(7) Uani 1 1 d . . C8 C 0.7183(3) 0.46425(11) 0.5192(3) 0.0628(7) Uani 1 1 d . . C7 C 0.7030(3) 0.51491(12) 0.4106(3) 0.0689(7) Uani 1 1 d . . N1 N 0.7301(3) 0.30856(12) 0.8084(3) 0.1040(9) Uani 1 1 d . . C4 C 0.4816(3) 0.41930(13) 0.3361(3) 0.0739(8) Uani 1 1 d . . C2 C 0.5769(3) 0.35821(12) 0.5476(3) 0.0717(7) Uani 1 1 d . . C15 C 1.0545(3) 0.50840(12) 0.8385(3) 0.0751(8) Uani 1 1 d . . H15 H 1.0609 0.4748 0.9025 0.090 Uiso 1 1 calc R U C17 C 0.2564(3) 0.33253(11) 0.0524(3) 0.0754(8) Uani 1 1 d . . C11 C 0.8142(3) 0.56201(11) 0.4519(3) 0.0721(8) Uani 1 1 d . . H11 H 0.8092 0.5944 0.3852 0.087 Uiso 1 1 calc R U C1 C 0.6651(3) 0.33217(12) 0.6922(4) 0.0789(8) Uani 1 1 d . . C23 C 0.4437(3) 0.33113(13) 0.4494(4) 0.0813(8) Uani 1 1 d . . H23 H 0.4014 0.2941 0.4674 0.098 Uiso 1 1 calc R U C6 C 0.5750(3) 0.51543(13) 0.2679(3) 0.0837(8) Uani 1 1 d . . H6 H 0.5668 0.5480 0.2008 0.100 Uiso 1 1 calc R U C12 C 1.0473(3) 0.60959(12) 0.6441(3) 0.0798(8) Uani 1 1 d . . H12 H 1.0470 0.6424 0.5800 0.096 Uiso 1 1 calc R U C5 C 0.4662(3) 0.46919(13) 0.2298(3) 0.0867(9) Uani 1 1 d . . H5 H 0.3859 0.4702 0.1388 0.104 Uiso 1 1 calc R U C14 C 1.1578(3) 0.55684(13) 0.8850(3) 0.0865(9) Uani 1 1 d . . H14 H 1.2294 0.5565 0.9814 0.104 Uiso 1 1 calc R U C22 C 0.3927(4) 0.31666(13) 0.0379(4) 0.0947(10) Uani 1 1 d . . H22 H 0.4822 0.3214 0.1190 0.114 Uiso 1 1 calc R U C13 C 1.1551(3) 0.60807(13) 0.7849(4) 0.0883(9) Uani 1 1 d . . H13 H 1.2263 0.6399 0.8160 0.106 Uiso 1 1 calc R U C18 C 0.1226(4) 0.32588(12) -0.0735(4) 0.0898(9) Uani 1 1 d . . H18 H 0.0314 0.3370 -0.0660 0.108 Uiso 1 1 calc R U C16 C 0.2413(3) 0.35564(14) 0.1975(3) 0.0912(9) Uani 1 1 d . . H16A H 0.1835 0.3943 0.1765 0.109 Uiso 1 1 calc R U H16B H 0.1846 0.3248 0.2296 0.109 Uiso 1 1 calc R U C21 C 0.3950(5) 0.29335(15) -0.0998(5) 0.1154(12) Uani 1 1 d . . H21 H 0.4857 0.2828 -0.1090 0.138 Uiso 1 1 calc R U C20 C 0.2595(7) 0.28620(16) -0.2224(5) 0.1221(15) Uani 1 1 d . . H20 H 0.2603 0.2702 -0.3125 0.146 Uiso 1 1 calc R U C19 C 0.1250(6) 0.30300(16) -0.2088(4) 0.1173(12) Uani 1 1 d . . H19 H 0.0356 0.2990 -0.2904 0.141 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 N2 0.0706(15) 0.0542(12) 0.0677(14) -0.0014(10) 0.0260(12) 0.0014(11) N3 0.0683(16) 0.0740(15) 0.0960(18) -0.0171(13) 0.0241(14) -0.0029(13) C9 0.0674(16) 0.0553(15) 0.0650(16) -0.0038(12) 0.0274(14) 0.0036(13) C3 0.0658(17) 0.0555(16) 0.0744(17) -0.0035(13) 0.0249(15) 0.0067(13) C10 0.0740(19) 0.0560(16) 0.0730(17) -0.0030(13) 0.0313(15) 0.0007(13) C8 0.0678(18) 0.0535(15) 0.0665(17) -0.0034(12) 0.0235(14) 0.0061(13) C7 0.0781(19) 0.0568(16) 0.0690(17) 0.0004(13) 0.0231(15) 0.0056(14) N1 0.091(2) 0.0955(19) 0.120(2) 0.0280(16) 0.0312(17) 0.0015(15) C4 0.0693(19) 0.0666(18) 0.0812(19) -0.0081(15) 0.0217(16) 0.0083(15) C2 0.0676(18) 0.0623(16) 0.0845(19) -0.0045(15) 0.0266(16) 0.0035(14) C15 0.0826(19) 0.0657(17) 0.0718(17) -0.0020(13) 0.0218(15) -0.0006(15) C17 0.0710(19) 0.0625(17) 0.091(2) -0.0097(14) 0.0276(17) -0.0040(14) C11 0.086(2) 0.0583(16) 0.0738(18) 0.0061(13) 0.0317(16) 0.0067(15) C1 0.072(2) 0.0633(18) 0.107(2) 0.0016(16) 0.0390(19) -0.0045(15) C23 0.078(2) 0.0683(18) 0.101(2) -0.0065(17) 0.0363(18) 0.0000(16) C6 0.098(2) 0.0709(18) 0.0727(18) 0.0070(14) 0.0199(17) 0.0152(17) C12 0.087(2) 0.0634(18) 0.092(2) 0.0014(14) 0.0364(18) -0.0027(15) C5 0.080(2) 0.079(2) 0.083(2) -0.0062(16) 0.0080(16) 0.0094(17) C14 0.080(2) 0.079(2) 0.085(2) -0.0076(16) 0.0114(16) -0.0030(17) C22 0.090(2) 0.084(2) 0.116(3) -0.0161(18) 0.045(2) 0.0002(17) C13 0.080(2) 0.0707(19) 0.109(2) -0.0107(17) 0.0282(19) -0.0121(16) C18 0.096(2) 0.077(2) 0.091(2) -0.0017(16) 0.027(2) -0.0075(16) C16 0.0605(19) 0.102(2) 0.104(2) -0.0281(17) 0.0209(18) 0.0008(16) C21 0.149(4) 0.083(2) 0.149(3) 0.009(2) 0.095(3) 0.016(2) C20 0.212(5) 0.079(2) 0.097(3) 0.011(2) 0.082(3) 0.005(3) C19 0.160(4) 0.095(3) 0.089(3) 0.004(2) 0.036(3) -0.008(3) 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C8 N2 C9 117.8(2) C23 N3 C4 108.3(2) C23 N3 C16 125.7(3) C4 N3 C16 125.9(3) N2 C9 C15 118.6(2) N2 C9 C10 123.2(2) C15 C9 C10 118.1(2) C4 C3 C8 120.2(2) C4 C3 C2 106.0(2) C8 C3 C2 133.8(2) C11 C10 C9 117.2(2) C11 C10 C12 123.8(2) C9 C10 C12 119.0(2) N2 C8 C3 120.0(2) N2 C8 C7 123.5(2) C3 C8 C7 116.5(2) C11 C7 C6 123.0(2) C11 C7 C8 116.9(2) C6 C7 C8 120.1(2) C3 C4 N3 108.8(2) C3 C4 C5 123.3(3) N3 C4 C5 127.9(3) C23 C2 C1 123.9(3) C23 C2 C3 106.9(2) C1 C2 C3 129.3(2) C14 C15 C9 121.1(3) C14 C15 H15 119.4 C9 C15 H15 119.4 C22 C17 C18 118.5(3) C22 C17 C16 124.4(3) C18 C17 C16 117.1(3) C7 C11 C10 121.4(2) C7 C11 H11 119.3 C10 C11 H11 119.3 N1 C1 C2 176.1(3) N3 C23 C2 110.0(3) N3 C23 H23 125.0 C2 C23 H23 125.0 C5 C6 C7 122.3(3) C5 C6 H6 118.9 C7 C6 H6 118.9 C13 C12 C10 121.3(3) C13 C12 H12 119.3 C10 C12 H12 119.3 C6 C5 C4 117.6(3) C6 C5 H5 121.2 C4 C5 H5 121.2 C15 C14 C13 120.6(3) C15 C14 H14 119.7 C13 C14 H14 119.7 C17 C22 C21 120.3(3) C17 C22 H22 119.8 C21 C22 H22 119.8 C12 C13 C14 119.9(3) C12 C13 H13 120.1 C14 C13 H13 120.1 C19 C18 C17 121.1(3) C19 C18 H18 119.4 C17 C18 H18 119.4 N3 C16 C17 115.2(2) N3 C16 H16A 108.5 C17 C16 H16A 108.5 N3 C16 H16B 108.5 C17 C16 H16B 108.5 H16A C16 H16B 107.5 C20 C21 C22 119.8(4) C20 C21 H21 120.1 C22 C21 H21 120.1 C19 C20 C21 119.8(4) C19 C20 H20 120.1 C21 C20 H20 120.1 C20 C19 C18 120.4(4) C20 C19 H19 119.8 C18 C19 H19 119.8 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance N2 C8 1.362(3) N2 C9 1.384(3) N3 C23 1.375(3) N3 C4 1.416(3) N3 C16 1.481(3) C9 C15 1.442(3) C9 C10 1.451(3) C3 C4 1.415(3) C3 C8 1.465(3) C3 C2 1.466(3) C10 C11 1.419(3) C10 C12 1.451(4) C8 C7 1.469(3) C7 C11 1.410(3) C7 C6 1.468(3) N1 C1 1.173(3) C4 C5 1.443(4) C2 C23 1.403(4) C2 C1 1.447(4) C15 C14 1.384(3) C15 H15 0.9300 C17 C22 1.400(4) C17 C18 1.411(4) C17 C16 1.531(4) C11 H11 0.9300 C23 H23 0.9300 C6 C5 1.381(4) C6 H6 0.9300 C12 C13 1.369(4) C12 H12 0.9300 C5 H5 0.9300 C14 C13 1.447(4) C14 H14 0.9300 C22 C21 1.417(4) C22 H22 0.9300 C13 H13 0.9300 C18 C19 1.392(5) C18 H18 0.9300 C16 H16A 0.9700 C16 H16B 0.9700 C21 C20 1.406(5) C21 H21 0.9300 C20 C19 1.385(5) C20 H20 0.9300 C19 H19 0.9300