#------------------------------------------------------------------------------ #$Date: 2020-05-01 03:51:24 +0300 (Fri, 01 May 2020) $ #$Revision: 251348 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/74/7157486.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_7157486 loop_ _publ_author_name 'Sreedharan, Ramdas' 'Rajeshwaran, Purushothaman' 'Panyam, Pradeep Kumar Reddy' 'Yadav, Saurabh' 'Nagaraja, C. M.' 'GANDHI, THIRUMANAVELAN' _publ_section_title ; Acylation of oxindoles using methyl/phenyl esters via mixed Claisen condensation -- An access to 3-alkylideneoxindoles ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/D0OB00789G _journal_year 2020 _chemical_formula_sum 'C16 H11 Br N O2' _chemical_formula_weight 329.17 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens geom _audit_block_doi 10.5517/ccdc.csd.cc23spj4 _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2019-10-18 deposited with the CCDC. 2020-04-30 downloaded from the CCDC. ; _cell_angle_alpha 83.964(5) _cell_angle_beta 73.197(5) _cell_angle_gamma 73.333(5) _cell_formula_units_Z 2 _cell_length_a 8.3268(14) _cell_length_b 9.2126(13) _cell_length_c 9.6765(16) _cell_measurement_temperature 273(2) _cell_volume 680.55(19) _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _diffrn_ambient_temperature 273(2) _diffrn_measured_fraction_theta_full 0.989 _diffrn_measured_fraction_theta_max 0.991 _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0521 _diffrn_reflns_av_unetI/netI 0.0362 _diffrn_reflns_Laue_measured_fraction_full 0.989 _diffrn_reflns_Laue_measured_fraction_max 0.991 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 12915 _diffrn_reflns_point_group_measured_fraction_full 0.989 _diffrn_reflns_point_group_measured_fraction_max 0.991 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.402 _diffrn_reflns_theta_min 2.199 _exptl_absorpt_coefficient_mu 3.020 _exptl_crystal_density_diffrn 1.606 _exptl_crystal_F_000 330 _refine_diff_density_max 0.652 _refine_diff_density_min -0.469 _refine_diff_density_rms 0.070 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 181 _refine_ls_number_reflns 2770 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.062 _refine_ls_R_factor_all 0.0404 _refine_ls_R_factor_gt 0.0370 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0543P)^2^+0.4185P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1032 _refine_ls_wR_factor_ref 0.1054 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2534 _reflns_number_total 2770 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ob00789g2.cif _cod_data_source_block shelx _cod_database_code 7157486 _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 SIR92 run in space group P -1 CELL 0.71073 8.3268 9.2126 9.6765 83.964 73.197 73.333 ZERR 2.00 0.0014 0.0013 0.0016 0.005 0.005 0.005 LATT 1 SFAC C H N O BR UNIT 32 22 2 4 2 MERG 2 FMAP 2 PLAN 25 ACTA CONF L.S. 10 TEMP 0.00 WGHT 0.054300 0.418500 FVAR 0.43239 BR1 5 0.865022 0.502030 0.872456 11.00000 0.07260 0.06357 = 0.04453 -0.00254 -0.02714 -0.02089 C1 1 0.700231 0.329694 0.303182 11.00000 0.05387 0.05963 = 0.03502 -0.00545 -0.01299 -0.01649 AFIX 33 H1A 2 0.680634 0.428513 0.257642 11.00000 -1.50000 H1B 2 0.795868 0.260356 0.240376 11.00000 -1.50000 H1C 2 0.597290 0.295233 0.322424 11.00000 -1.50000 AFIX 0 C2 1 0.775554 0.214848 0.528312 11.00000 0.05026 0.03512 = 0.04454 0.00096 -0.01360 -0.01325 N1 3 0.740767 0.337197 0.437442 11.00000 0.04608 0.03685 = 0.03474 0.00005 -0.01216 -0.01419 O2 4 0.521259 0.333537 0.814930 11.00000 0.04198 0.06577 = 0.06490 0.02394 -0.01154 -0.00505 C8 1 0.782381 0.695748 0.636615 11.00000 0.04481 0.03636 = 0.05207 -0.00671 -0.00754 -0.01428 AFIX 43 H8 2 0.794702 0.772566 0.684568 11.00000 -1.20000 AFIX 0 C11 1 0.708274 0.123981 0.900858 11.00000 0.04242 0.03340 = 0.03683 0.00451 -0.01439 -0.01711 C4 1 0.793433 0.434242 0.622202 11.00000 0.03597 0.03235 = 0.03302 0.00362 -0.00839 -0.01169 O1 4 0.776642 0.086756 0.508339 11.00000 0.10578 0.03685 = 0.07208 -0.00118 -0.03480 -0.02593 C5 1 0.749461 0.468855 0.492062 11.00000 0.03314 0.03430 = 0.03146 0.00153 -0.00716 -0.01059 C9 1 0.809454 0.548457 0.693704 11.00000 0.03675 0.04069 = 0.03703 -0.00041 -0.00903 -0.01197 C3 1 0.808696 0.269786 0.659095 11.00000 0.04199 0.03283 = 0.03797 0.00638 -0.01297 -0.01230 C10 1 0.665216 0.249257 0.796073 11.00000 0.03927 0.03904 = 0.04194 0.00813 -0.01503 -0.01391 C12 1 0.595638 0.132572 1.039916 11.00000 0.04853 0.04609 = 0.04017 0.00139 -0.00910 -0.01370 AFIX 43 H12 2 0.498616 0.215383 1.064561 11.00000 -1.20000 AFIX 0 C6 1 0.719234 0.614596 0.433200 11.00000 0.04257 0.03964 = 0.03662 0.00936 -0.00858 -0.01161 AFIX 43 H6 2 0.688205 0.636571 0.346865 11.00000 -1.20000 AFIX 0 C16 1 0.851328 0.000193 0.864851 11.00000 0.05382 0.03554 = 0.04273 0.00451 -0.00997 -0.01332 AFIX 43 H16 2 0.927563 -0.006380 0.772620 11.00000 -1.20000 AFIX 0 C14 1 0.770250 -0.103337 1.103816 11.00000 0.07453 0.04315 = 0.05086 0.01825 -0.02285 -0.02304 AFIX 43 H14 2 0.792295 -0.179604 1.172297 11.00000 -1.20000 AFIX 0 C13 1 0.627606 0.018895 1.140781 11.00000 0.06672 0.05694 = 0.03734 0.00878 -0.00984 -0.02837 AFIX 43 H13 2 0.552748 0.025017 1.233577 11.00000 -1.20000 AFIX 0 C7 1 0.737271 0.726559 0.508707 11.00000 0.04716 0.03205 = 0.05177 0.00782 -0.00830 -0.01116 AFIX 43 H7 2 0.718218 0.825385 0.471506 11.00000 -1.20000 AFIX 0 C15 1 0.880699 -0.114440 0.967173 11.00000 0.06673 0.03530 = 0.05792 0.00941 -0.01457 -0.00729 AFIX 43 H15 2 0.975632 -0.199004 0.942869 11.00000 -1.20000 AFIX 0 HKLF 4 REM SIR92 run in space group P -1 REM R1 = 0.0370 for 2534 Fo > 4sig(Fo) and 0.0404 for all 2770 data REM 181 parameters refined using 0 restraints END WGHT 0.0543 0.4185 REM Highest difference peak 0.652, deepest hole -0.469, 1-sigma level 0.070 Q1 1 0.9220 0.2167 0.6637 11.00000 0.05 0.65 Q2 1 0.5846 0.3966 0.3080 11.00000 0.05 0.46 Q3 1 0.7823 0.3756 0.2174 11.00000 0.05 0.43 Q4 1 0.7611 0.4957 0.9023 11.00000 0.05 0.42 Q5 1 0.7854 0.4982 0.1307 11.00000 0.05 0.38 Q6 1 0.8350 0.5863 0.8329 11.00000 0.05 0.37 Q7 1 0.7035 0.2209 0.2918 11.00000 0.05 0.37 Q8 1 0.5422 0.4981 0.8584 11.00000 0.05 0.34 Q9 1 0.9151 0.3806 0.8724 11.00000 0.05 0.31 Q10 1 0.6359 0.1181 0.9516 11.00000 0.05 0.27 Q11 1 0.6786 0.1735 0.8447 11.00000 0.05 0.25 Q12 1 0.7984 0.3613 0.6480 11.00000 0.05 0.25 Q13 1 0.7958 -0.1127 1.0227 11.00000 0.05 0.23 Q14 1 0.7568 0.2615 0.7124 11.00000 0.05 0.23 Q15 1 0.7610 0.6264 0.6646 11.00000 0.05 0.23 Q16 1 0.6888 0.5441 0.4774 11.00000 0.05 0.22 Q17 1 0.6538 0.0865 1.0909 11.00000 0.05 0.20 Q18 1 0.8324 0.6189 0.6430 11.00000 0.05 0.20 Q19 1 0.9025 0.0848 0.9261 11.00000 0.05 0.20 Q20 1 0.8463 -0.0693 0.9064 11.00000 0.05 0.19 Q21 1 0.5703 0.3626 0.8550 11.00000 0.05 0.19 Q22 1 0.9448 0.3021 0.8214 11.00000 0.05 0.19 Q23 1 0.9343 0.1272 0.8743 11.00000 0.05 0.18 Q24 1 0.7700 -0.1455 1.1127 11.00000 0.05 0.18 Q25 1 0.7493 0.4596 0.5665 11.00000 0.05 0.18 ; _shelx_res_checksum 26915 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 _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.86502(4) 0.50203(4) 0.87246(3) 0.05713(15) Uani 1 1 d . . . . . C1 C 0.7002(4) 0.3297(4) 0.3032(3) 0.0487(6) Uani 1 1 d . . . . . H1A H 0.6806 0.4285 0.2576 0.073 Uiso 1 1 calc R U . . . H1B H 0.7959 0.2604 0.2404 0.073 Uiso 1 1 calc R U . . . H1C H 0.5973 0.2952 0.3224 0.073 Uiso 1 1 calc R U . . . C2 C 0.7756(4) 0.2148(3) 0.5283(3) 0.0429(6) Uani 1 1 d . . . . . N1 N 0.7408(3) 0.3372(2) 0.4374(2) 0.0384(4) Uani 1 1 d . . . . . O2 O 0.5213(3) 0.3335(3) 0.8149(3) 0.0622(6) Uani 1 1 d . . . . . C8 C 0.7824(3) 0.6957(3) 0.6366(3) 0.0445(6) Uani 1 1 d . . . . . H8 H 0.7947 0.7726 0.6846 0.053 Uiso 1 1 calc R U . . . C11 C 0.7083(3) 0.1240(3) 0.9009(3) 0.0357(5) Uani 1 1 d . . . . . C4 C 0.7934(3) 0.4342(3) 0.6222(3) 0.0338(5) Uani 1 1 d . . . . . O1 O 0.7766(4) 0.0868(2) 0.5083(3) 0.0678(7) Uani 1 1 d . . . . . C5 C 0.7495(3) 0.4689(3) 0.4921(2) 0.0332(5) Uani 1 1 d . . . . . C9 C 0.8095(3) 0.5485(3) 0.6937(3) 0.0381(5) Uani 1 1 d . . . . . C3 C 0.8087(3) 0.2698(3) 0.6591(3) 0.0372(5) Uani 1 1 d . . . . . C10 C 0.6652(3) 0.2493(3) 0.7961(3) 0.0392(5) Uani 1 1 d . . . . . C12 C 0.5956(4) 0.1326(3) 1.0399(3) 0.0456(6) Uani 1 1 d . . . . . H12 H 0.4986 0.2154 1.0646 0.055 Uiso 1 1 calc R U . . . C6 C 0.7192(3) 0.6146(3) 0.4332(3) 0.0408(5) Uani 1 1 d . . . . . H6 H 0.6882 0.6366 0.3469 0.049 Uiso 1 1 calc R U . . . C16 C 0.8513(4) 0.0002(3) 0.8649(3) 0.0449(6) Uani 1 1 d . . . . . H16 H 0.9276 -0.0064 0.7726 0.054 Uiso 1 1 calc R U . . . C14 C 0.7703(4) -0.1033(3) 1.1038(3) 0.0548(7) Uani 1 1 d . . . . . H14 H 0.7923 -0.1796 1.1723 0.066 Uiso 1 1 calc R U . . . C13 C 0.6276(4) 0.0189(3) 1.1408(3) 0.0528(7) Uani 1 1 d . . . . . H13 H 0.5527 0.0250 1.2336 0.063 Uiso 1 1 calc R U . . . C7 C 0.7373(3) 0.7266(3) 0.5087(3) 0.0454(6) Uani 1 1 d . . . . . H7 H 0.7182 0.8254 0.4715 0.054 Uiso 1 1 calc R U . . . C15 C 0.8807(4) -0.1144(3) 0.9672(4) 0.0560(8) Uani 1 1 d . . . . . H15 H 0.9756 -0.1990 0.9429 0.067 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 Br1 0.0726(2) 0.0636(2) 0.04453(19) -0.00254(13) -0.02714(15) -0.02089(16) C1 0.0539(15) 0.0596(17) 0.0350(13) -0.0054(11) -0.0130(11) -0.0165(13) C2 0.0503(14) 0.0351(13) 0.0445(14) 0.0010(10) -0.0136(11) -0.0133(11) N1 0.0461(11) 0.0368(11) 0.0347(10) 0.0000(8) -0.0122(9) -0.0142(9) O2 0.0420(11) 0.0658(14) 0.0649(14) 0.0239(11) -0.0115(10) -0.0051(10) C8 0.0448(14) 0.0364(13) 0.0521(15) -0.0067(11) -0.0075(11) -0.0143(11) C11 0.0424(12) 0.0334(12) 0.0368(12) 0.0045(9) -0.0144(10) -0.0171(10) C4 0.0360(11) 0.0323(11) 0.0330(11) 0.0036(9) -0.0084(9) -0.0117(9) O1 0.1058(19) 0.0368(11) 0.0721(15) -0.0012(10) -0.0348(14) -0.0259(12) C5 0.0331(11) 0.0343(11) 0.0315(11) 0.0015(9) -0.0072(9) -0.0106(9) C9 0.0367(12) 0.0407(13) 0.0370(12) -0.0004(10) -0.0090(10) -0.0120(10) C3 0.0420(12) 0.0328(12) 0.0380(12) 0.0064(9) -0.0130(10) -0.0123(10) C10 0.0393(13) 0.0390(13) 0.0419(13) 0.0081(10) -0.0150(10) -0.0139(10) C12 0.0485(14) 0.0461(15) 0.0402(14) 0.0014(11) -0.0091(11) -0.0137(12) C6 0.0426(13) 0.0396(13) 0.0366(12) 0.0094(10) -0.0086(10) -0.0116(10) C16 0.0538(15) 0.0355(13) 0.0427(14) 0.0045(11) -0.0100(12) -0.0133(12) C14 0.075(2) 0.0431(15) 0.0509(16) 0.0183(12) -0.0229(15) -0.0230(14) C13 0.0667(19) 0.0569(17) 0.0373(14) 0.0088(12) -0.0098(13) -0.0284(15) C7 0.0472(14) 0.0321(12) 0.0518(16) 0.0078(11) -0.0083(12) -0.0112(11) C15 0.0667(19) 0.0353(14) 0.0579(18) 0.0094(12) -0.0146(15) -0.0073(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' Br Br -0.2901 2.4595 '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 O1 C2 N1 125.3(3) . . ? O1 C2 C3 126.7(3) . . ? N1 C2 C3 108.0(2) . . ? C2 N1 C5 111.1(2) . . ? C2 N1 C1 123.9(2) . . ? C5 N1 C1 125.0(2) . . ? C7 C8 C9 119.3(2) . . ? C16 C11 C12 119.5(2) . . ? C16 C11 C10 122.8(2) . . ? C12 C11 C10 117.7(2) . . ? C9 C4 C5 118.8(2) . . ? C9 C4 C3 132.2(2) . . ? C5 C4 C3 109.0(2) . . ? C6 C5 C4 122.2(2) . . ? C6 C5 N1 128.2(2) . . ? C4 C5 N1 109.5(2) . . ? C4 C9 C8 120.5(2) . . ? C4 C9 Br1 118.74(19) . . ? C8 C9 Br1 120.8(2) . . ? C4 C3 C2 102.30(19) . . ? C4 C3 C10 111.0(2) . . ? C2 C3 C10 109.2(2) . . ? O2 C10 C11 121.6(2) . . ? O2 C10 C3 119.3(2) . . ? C11 C10 C3 119.1(2) . . ? C13 C12 C11 120.2(3) . . ? C5 C6 C7 117.1(2) . . ? C11 C16 C15 119.6(3) . . ? C15 C14 C13 120.8(3) . . ? C14 C13 C12 119.7(3) . . ? C8 C7 C6 122.0(2) . . ? C14 C15 C16 120.2(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 Br1 C9 1.893(3) . ? C1 N1 1.446(3) . ? C2 O1 1.213(3) . ? C2 N1 1.371(3) . ? C2 C3 1.533(4) . ? N1 C5 1.401(3) . ? O2 C10 1.201(3) . ? C8 C7 1.374(4) . ? C8 C9 1.391(4) . ? C11 C16 1.380(4) . ? C11 C12 1.395(4) . ? C11 C10 1.488(3) . ? C4 C9 1.375(3) . ? C4 C5 1.392(3) . ? C4 C3 1.497(3) . ? C5 C6 1.385(3) . ? C3 C10 1.543(3) . ? C12 C13 1.377(4) . ? C6 C7 1.390(4) . ? C16 C15 1.388(4) . ? C14 C15 1.370(4) . ? C14 C13 1.371(4) . ? 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C2 N1 C5 179.8(3) . . . . ? C3 C2 N1 C5 0.9(3) . . . . ? O1 C2 N1 C1 -0.1(5) . . . . ? C3 C2 N1 C1 -179.0(2) . . . . ? C9 C4 C5 C6 -0.8(4) . . . . ? C3 C4 C5 C6 177.3(2) . . . . ? C9 C4 C5 N1 179.7(2) . . . . ? C3 C4 C5 N1 -2.1(3) . . . . ? C2 N1 C5 C6 -178.6(2) . . . . ? C1 N1 C5 C6 1.3(4) . . . . ? C2 N1 C5 C4 0.8(3) . . . . ? C1 N1 C5 C4 -179.3(2) . . . . ? C5 C4 C9 C8 -0.1(4) . . . . ? C3 C4 C9 C8 -177.7(2) . . . . ? C5 C4 C9 Br1 178.84(17) . . . . ? C3 C4 C9 Br1 1.3(4) . . . . ? C7 C8 C9 C4 0.8(4) . . . . ? C7 C8 C9 Br1 -178.12(19) . . . . ? C9 C4 C3 C2 -179.7(3) . . . . ? C5 C4 C3 C2 2.5(3) . . . . ? C9 C4 C3 C10 63.9(3) . . . . ? C5 C4 C3 C10 -113.8(2) . . . . ? O1 C2 C3 C4 179.1(3) . . . . ? N1 C2 C3 C4 -2.0(3) . . . . ? O1 C2 C3 C10 -63.3(4) . . . . ? N1 C2 C3 C10 115.6(2) . . . . ? C16 C11 C10 O2 160.1(3) . . . . ? C12 C11 C10 O2 -18.5(4) . . . . ? C16 C11 C10 C3 -19.2(4) . . . . ? C12 C11 C10 C3 162.2(2) . . . . ? C4 C3 C10 O2 38.4(4) . . . . ? C2 C3 C10 O2 -73.6(3) . . . . ? C4 C3 C10 C11 -142.4(2) . . . . ? C2 C3 C10 C11 105.6(3) . . . . ? C16 C11 C12 C13 0.4(4) . . . . ? C10 C11 C12 C13 179.1(3) . . . . ? C4 C5 C6 C7 1.0(4) . . . . ? N1 C5 C6 C7 -179.7(2) . . . . ? C12 C11 C16 C15 0.3(4) . . . . ? C10 C11 C16 C15 -178.2(3) . . . . ? C15 C14 C13 C12 -0.6(5) . . . . ? C11 C12 C13 C14 -0.3(4) . . . . ? C9 C8 C7 C6 -0.6(4) . . . . ? C5 C6 C7 C8 -0.3(4) . . . . ? C13 C14 C15 C16 1.4(5) . . . . ? C11 C16 C15 C14 -1.3(5) . . . . ?