#------------------------------------------------------------------------------ #$Date: 2015-01-29 01:01:33 +0200 (Thu, 29 Jan 2015) $ #$Revision: 130193 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/98/2019808.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2019808 loop_ _publ_author_name 'Shreevidhyaa Suressh, V.' 'Prathebha, K.' 'Abdul Basheer, S.' 'Ponnuswamy, S.' 'Usha, G.' _publ_section_title ; Crystal structure of 2-chloro-1-(3-methyl-2,6-diphenylpiperidin-1-yl)ethanone ; _journal_issue 2 _journal_name_full 'Acta Crystallographica Section E Crystallographic Communications' _journal_page_first o135 _journal_paper_doi 10.1107/S205698901500122X _journal_volume 71 _journal_year 2015 _chemical_formula_iupac 'C20 H22 Cl N O' _chemical_formula_moiety 'C20 H22 Cl N O' _chemical_formula_sum 'C20 H22 Cl N O' _chemical_formula_weight 327.84 _chemical_name_systematic ; 2-Chloro-1-(3-methyl-2,6-diphenylpiperidin-1-yl)ethanone ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 101.523(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 8.7146(3) _cell_length_b 12.3963(4) _cell_length_c 16.6117(6) _cell_measurement_reflns_used 4353 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 28.2 _cell_measurement_theta_min 2.1 _cell_volume 1758.37(11) _computing_cell_refinement ; SAINT (Bruker, 2008) ; _computing_data_collection ; APEX2 (Bruker, 2008) ; _computing_data_reduction ; SAINT (Bruker, 2008) ; _computing_molecular_graphics ; ORTEP-3 for Windows (Farrugia, 2012) ; _computing_publication_material ; SHELXL97 (Sheldrick, 2015) and PLATON (Spek, 2009) ; _computing_structure_refinement ; SHELXL97 (Sheldrick, 2015) ; _computing_structure_solution ; SHELXS97 (Sheldrick, 2008) ; _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measurement_device_type 'Bruker APEXII CCD' _diffrn_measurement_method '\w and \f scan' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0258 _diffrn_reflns_av_sigmaI/netI 0.0234 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 16473 _diffrn_reflns_theta_full 28.23 _diffrn_reflns_theta_max 28.23 _diffrn_reflns_theta_min 2.07 _exptl_absorpt_coefficient_mu 0.222 _exptl_absorpt_correction_T_max 0.950 _exptl_absorpt_correction_T_min 0.946 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; (SADABS; Bruker, 2008) ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.238 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 696 _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.23 _refine_diff_density_max 0.472 _refine_diff_density_min -0.375 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.915 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 208 _refine_ls_number_reflns 4353 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.915 _refine_ls_R_factor_all 0.0720 _refine_ls_R_factor_gt 0.0503 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1971 _refine_ls_wR_factor_ref 0.2363 _reflns_number_gt 3075 _reflns_number_total 4353 _reflns_threshold_expression >2sigma(I) _iucr_refine_instructions_details ; TITL USHA_CA3MP_0m in P2(1)/n CELL 0.71073 8.7146 12.3963 16.6117 90.000 101.523 90.000 ZERR 4.00 0.0003 0.0004 0.0006 0.000 0.002 0.000 LATT 1 SYMM 1/2 - X, 1/2 + Y, 1/2 - Z SFAC C H N O CL UNIT 80 88 4 4 4 ACTA CONF BOND $H WPDB MERG 2 FMAP 2 PLAN 20 BOND L.S. 30 WGHT 0.200000 FVAR 0.22120 C17 1 0.626857 0.826302 0.424120 11.00000 0.05616 0.04720 = 0.05364 0.00011 0.00413 -0.00819 AFIX 43 H17 2 0.650697 0.899505 0.426431 11.00000 -1.20000 AFIX 0 MOLE 1 C1 1 0.308300 0.976095 0.302560 11.00000 0.04310 0.05737 = 0.04788 0.00087 0.00692 0.00113 C2 1 0.202631 0.880937 0.311115 11.00000 0.04483 0.06837 = 0.06040 0.01063 0.01057 -0.00213 AFIX 23 H2A 2 0.139953 0.897151 0.351719 11.00000 -1.20000 H2B 2 0.265676 0.817713 0.329273 11.00000 -1.20000 AFIX 0 C3 1 0.463914 1.094854 0.112673 11.00000 0.15590 0.11198 = 0.05105 0.01712 0.00996 0.04640 AFIX 33 H3A 2 0.450826 1.168031 0.128980 11.00000 -1.50000 H3B 2 0.365694 1.057529 0.106231 11.00000 -1.50000 H3C 2 0.499083 1.094333 0.061470 11.00000 -1.50000 AFIX 0 C4 1 0.539450 1.051085 0.262958 11.00000 0.04635 0.03888 = 0.04306 0.00211 0.01006 -0.00003 AFIX 13 H4 2 0.466028 1.111796 0.257092 11.00000 -1.20000 AFIX 0 C5 1 0.670525 1.081018 0.334762 11.00000 0.04707 0.03266 = 0.04550 0.00037 0.01096 -0.00171 C6 1 0.629207 1.133992 0.400662 11.00000 0.05086 0.06322 = 0.05183 -0.00844 0.01384 0.00606 AFIX 43 H6 2 0.523981 1.147046 0.400296 11.00000 -1.20000 AFIX 0 C7 1 0.740860 1.167860 0.466918 11.00000 0.07163 0.07929 = 0.05058 -0.01647 0.00794 0.00734 AFIX 43 H7 2 0.710238 1.203948 0.510199 11.00000 -1.20000 AFIX 0 C8 1 0.896255 1.148635 0.469259 11.00000 0.06127 0.07150 = 0.06227 -0.00862 -0.00456 -0.00368 AFIX 43 H8 2 0.971284 1.170729 0.514203 11.00000 -1.20000 AFIX 0 C9 1 0.940362 1.096457 0.404682 11.00000 0.04773 0.05698 = 0.07721 -0.00956 0.00617 -0.00195 AFIX 43 H9 2 1.045841 1.082948 0.406099 11.00000 -1.20000 AFIX 0 C10 1 0.829197 1.063645 0.337291 11.00000 0.04940 0.04367 = 0.06012 -0.00700 0.01389 -0.00149 AFIX 43 H10 2 0.860962 1.029747 0.293421 11.00000 -1.20000 AFIX 0 C12 1 0.584345 1.038974 0.178057 11.00000 0.06678 0.05457 = 0.04467 0.00254 0.01505 -0.00377 AFIX 13 H12 2 0.684272 1.076430 0.180741 11.00000 -1.20000 AFIX 0 C13 1 0.607531 0.923721 0.154529 11.00000 0.09930 0.06014 = 0.05021 -0.00542 0.03054 0.00330 AFIX 23 H13A 2 0.513440 0.898621 0.117842 11.00000 -1.20000 H13B 2 0.692876 0.920455 0.125013 11.00000 -1.20000 AFIX 0 C14 1 0.643952 0.849090 0.228779 11.00000 0.06982 0.04486 = 0.05783 -0.00362 0.02694 0.00540 AFIX 23 H14A 2 0.736017 0.874992 0.266649 11.00000 -1.20000 H14B 2 0.666131 0.777158 0.211146 11.00000 -1.20000 AFIX 0 C15 1 0.505298 0.844908 0.272121 11.00000 0.04721 0.03845 = 0.04653 -0.00449 0.00572 -0.00354 AFIX 13 H15 2 0.420792 0.805887 0.235962 11.00000 -1.20000 AFIX 0 C16 1 0.547249 0.781223 0.351332 11.00000 0.03950 0.04269 = 0.04958 -0.00168 0.00891 -0.00135 C18 1 0.671282 0.762374 0.493816 11.00000 0.05205 0.07153 = 0.05283 0.00430 0.00138 -0.00547 AFIX 43 H18 2 0.725299 0.793164 0.542318 11.00000 -1.20000 AFIX 0 C19 1 0.636385 0.655226 0.491623 11.00000 0.06078 0.06582 = 0.06482 0.02115 0.01594 0.00567 AFIX 43 H19 2 0.667295 0.613021 0.538336 11.00000 -1.20000 AFIX 0 C20 1 0.554877 0.609198 0.419812 11.00000 0.08196 0.04488 = 0.07486 0.01027 0.02450 -0.00323 AFIX 43 H20 2 0.530018 0.536173 0.418408 11.00000 -1.20000 AFIX 0 C21 1 0.510150 0.672072 0.349779 11.00000 0.05999 0.04245 = 0.05804 -0.00141 0.01343 -0.00596 AFIX 43 H21 2 0.455127 0.640970 0.301638 11.00000 -1.20000 AFIX 0 N1 3 0.447968 0.955703 0.281959 11.00000 0.04223 0.04176 = 0.04448 0.00029 0.00813 -0.00195 O1 4 0.259292 1.066172 0.313593 11.00000 0.05232 0.06398 = 0.08630 -0.00411 0.02052 0.00954 CL1 5 0.078780 0.855120 0.214696 11.00000 0.07287 0.08201 = 0.08124 -0.00080 -0.01206 -0.01882 HKLF 4 REM USHA_CA3MP_0m in P2(1)/n REM R1 = 0.0503 for 3075 Fo > 4sig(Fo) and 0.0720 for all 4335 data REM 208 parameters refined using 0 restraints END WGHT 0.0749 0.4320 REM Highest difference peak 0.472, deepest hole -0.375, 1-sigma level 0.051 Q1 1 0.0337 0.8545 0.2740 11.00000 0.05 0.47 Q2 1 0.6573 0.8020 0.3943 11.00000 0.05 0.22 Q3 1 0.6239 0.7975 0.4647 11.00000 0.05 0.19 Q4 1 0.4919 1.0034 0.2760 11.00000 0.05 0.19 Q5 1 0.5585 0.6493 0.4724 11.00000 0.05 0.19 Q6 1 0.6123 1.0595 0.3009 11.00000 0.05 0.18 Q7 1 0.6542 1.1146 0.3680 11.00000 0.05 0.17 Q8 1 0.5393 1.1409 0.1364 11.00000 0.05 0.17 Q9 1 0.5775 0.8398 0.2527 11.00000 0.05 0.17 Q10 1 0.2324 0.8269 0.2819 11.00000 0.05 0.16 Q11 1 0.6419 0.6272 0.4479 11.00000 0.05 0.16 Q12 1 0.6166 0.8981 0.1089 11.00000 0.05 0.16 Q13 1 0.7235 0.7602 0.4577 11.00000 0.05 0.16 Q14 1 0.5276 0.6466 0.3846 11.00000 0.05 0.16 Q15 1 0.6946 0.7002 0.4751 11.00000 0.05 0.16 Q16 1 0.2488 1.0225 0.2773 11.00000 0.05 0.15 Q17 1 0.2639 0.9344 0.3022 11.00000 0.05 0.15 Q18 1 0.5692 1.0435 0.2251 11.00000 0.05 0.15 Q19 1 0.7315 1.2005 0.4729 11.00000 0.05 0.15 Q20 1 0.7306 1.0775 0.3283 11.00000 0.05 0.14 ; _[local]_cod_data_source_file su5068sup1.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/n' _cod_original_cell_volume 1758.37(10) _cod_database_code 2019808 loop_ _symmetry_equiv_pos_as_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_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_symmetry_multiplicity C C17 0.6269(2) 0.82630(15) 0.42412(12) 0.0533(5) Uani d . 1 1 H H17 0.6507 0.8995 0.4264 0.064 Uiso calc R 1 1 C C1 0.3083(2) 0.97610(15) 0.30256(11) 0.0498(4) Uani d . 1 1 C C2 0.2026(2) 0.88094(17) 0.31112(13) 0.0579(5) Uani d . 1 1 H H2A 0.1400 0.8972 0.3517 0.069 Uiso calc R 1 1 H H2B 0.2657 0.8177 0.3293 0.069 Uiso calc R 1 1 C C3 0.4639(5) 1.0949(3) 0.11267(17) 0.1078(11) Uani d . 1 1 H H3A 0.4508 1.1680 0.1290 0.162 Uiso calc R 1 1 H H3B 0.3657 1.0575 0.1062 0.162 Uiso calc R 1 1 H H3C 0.4991 1.0943 0.0615 0.162 Uiso calc R 1 1 C C4 0.53945(19) 1.05108(12) 0.26296(10) 0.0426(4) Uani d . 1 1 H H4 0.4660 1.1118 0.2571 0.051 Uiso calc R 1 1 C C5 0.67052(19) 1.08102(12) 0.33476(10) 0.0415(4) Uani d . 1 1 C C6 0.6292(2) 1.13399(16) 0.40066(12) 0.0548(5) Uani d . 1 1 H H6 0.5240 1.1470 0.4003 0.066 Uiso calc R 1 1 C C7 0.7409(3) 1.16786(19) 0.46692(14) 0.0678(6) Uani d . 1 1 H H7 0.7102 1.2039 0.5102 0.081 Uiso calc R 1 1 C C8 0.8963(3) 1.14864(17) 0.46926(15) 0.0674(6) Uani d . 1 1 H H8 0.9713 1.1707 0.5142 0.081 Uiso calc R 1 1 C C9 0.9404(2) 1.09646(16) 0.40468(14) 0.0615(5) Uani d . 1 1 H H9 1.0458 1.0829 0.4061 0.074 Uiso calc R 1 1 C C10 0.8292(2) 1.06365(14) 0.33729(12) 0.0507(4) Uani d . 1 1 H H10 0.8610 1.0297 0.2934 0.061 Uiso calc R 1 1 C C12 0.5843(2) 1.03897(16) 0.17806(11) 0.0548(5) Uani d . 1 1 H H12 0.6843 1.0764 0.1807 0.066 Uiso calc R 1 1 C C13 0.6075(3) 0.92372(16) 0.15453(13) 0.0677(6) Uani d . 1 1 H H13A 0.5134 0.8986 0.1178 0.081 Uiso calc R 1 1 H H13B 0.6929 0.9205 0.1250 0.081 Uiso calc R 1 1 C C14 0.6440(3) 0.84909(14) 0.22878(13) 0.0555(5) Uani d . 1 1 H H14A 0.7360 0.8750 0.2666 0.067 Uiso calc R 1 1 H H14B 0.6661 0.7772 0.2111 0.067 Uiso calc R 1 1 C C15 0.5053(2) 0.84491(12) 0.27212(11) 0.0446(4) Uani d . 1 1 H H15 0.4208 0.8059 0.2360 0.053 Uiso calc R 1 1 C C16 0.54725(18) 0.78122(13) 0.35133(10) 0.0439(4) Uani d . 1 1 C C18 0.6713(2) 0.76237(18) 0.49382(13) 0.0601(5) Uani d . 1 1 H H18 0.7253 0.7932 0.5423 0.072 Uiso calc R 1 1 C C19 0.6364(3) 0.65523(18) 0.49162(15) 0.0633(5) Uani d . 1 1 H H19 0.6673 0.6130 0.5383 0.076 Uiso calc R 1 1 C C20 0.5549(3) 0.60920(16) 0.41981(15) 0.0660(6) Uani d . 1 1 H H20 0.5300 0.5362 0.4184 0.079 Uiso calc R 1 1 C C21 0.5101(2) 0.67207(14) 0.34978(13) 0.0533(5) Uani d . 1 1 H H21 0.4551 0.6410 0.3016 0.064 Uiso calc R 1 1 N N1 0.44797(15) 0.95570(11) 0.28196(8) 0.0429(4) Uani d . 1 1 O O1 0.25929(16) 1.06617(12) 0.31359(10) 0.0666(4) Uani d . 1 1 Cl Cl1 0.07878(7) 0.85512(5) 0.21470(4) 0.0825(3) Uani d . 1 1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 C17 0.0562(11) 0.0472(10) 0.0536(11) -0.0082(8) 0.0041(8) 0.0001(8) C1 0.0431(9) 0.0574(10) 0.0479(9) 0.0011(7) 0.0069(7) 0.0009(8) C2 0.0448(9) 0.0684(12) 0.0604(12) -0.0021(8) 0.0106(8) 0.0106(9) C3 0.156(3) 0.112(2) 0.0510(14) 0.046(2) 0.0100(16) 0.0171(14) C4 0.0463(8) 0.0389(8) 0.0431(9) 0.0000(6) 0.0101(7) 0.0021(6) C5 0.0471(8) 0.0327(7) 0.0455(9) -0.0017(6) 0.0110(7) 0.0004(6) C6 0.0509(10) 0.0632(11) 0.0518(11) 0.0061(8) 0.0138(8) -0.0084(8) C7 0.0716(14) 0.0793(14) 0.0506(11) 0.0073(11) 0.0079(10) -0.0165(10) C8 0.0613(12) 0.0715(13) 0.0623(13) -0.0037(10) -0.0046(10) -0.0086(10) C9 0.0477(10) 0.0570(11) 0.0772(14) -0.0019(8) 0.0062(9) -0.0096(10) C10 0.0494(9) 0.0437(9) 0.0601(11) -0.0015(7) 0.0139(8) -0.0070(8) C12 0.0668(12) 0.0546(11) 0.0447(10) -0.0038(8) 0.0151(8) 0.0025(8) C13 0.0993(16) 0.0601(12) 0.0502(11) 0.0033(11) 0.0305(11) -0.0054(9) C14 0.0698(12) 0.0449(9) 0.0578(11) 0.0054(8) 0.0269(9) -0.0036(8) C15 0.0472(9) 0.0385(8) 0.0465(9) -0.0035(6) 0.0057(7) -0.0045(6) C16 0.0395(8) 0.0427(8) 0.0496(9) -0.0013(6) 0.0089(7) -0.0017(7) C18 0.0521(10) 0.0715(13) 0.0528(11) -0.0055(9) 0.0014(8) 0.0043(9) C19 0.0608(12) 0.0658(12) 0.0648(13) 0.0057(9) 0.0159(10) 0.0212(10) C20 0.0820(15) 0.0449(10) 0.0749(14) -0.0032(9) 0.0245(12) 0.0103(9) C21 0.0600(11) 0.0424(9) 0.0580(11) -0.0060(7) 0.0134(9) -0.0014(8) N1 0.0422(7) 0.0418(7) 0.0445(8) -0.0020(5) 0.0081(6) 0.0003(6) O1 0.0523(8) 0.0640(9) 0.0863(11) 0.0095(6) 0.0205(7) -0.0041(7) Cl1 0.0729(4) 0.0820(5) 0.0812(5) -0.0188(3) -0.0121(3) -0.0008(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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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 C16 C17 C18 120.23(17) C16 C17 H17 119.9 C18 C17 H17 119.9 O1 C1 N1 124.60(17) O1 C1 C2 117.28(17) N1 C1 C2 118.11(16) C1 C2 Cl1 109.05(13) C1 C2 H2A 109.9 Cl1 C2 H2A 109.9 C1 C2 H2B 109.9 Cl1 C2 H2B 109.9 H2A C2 H2B 108.3 C12 C3 H3A 109.5 C12 C3 H3B 109.5 H3A C3 H3B 109.5 C12 C3 H3C 109.5 H3A C3 H3C 109.5 H3B C3 H3C 109.5 N1 C4 C5 112.06(13) N1 C4 C12 111.04(13) C5 C4 C12 116.84(14) N1 C4 H4 105.3 C5 C4 H4 105.3 C12 C4 H4 105.3 C6 C5 C10 117.60(16) C6 C5 C4 117.51(15) C10 C5 C4 124.82(15) C7 C6 C5 121.42(18) C7 C6 H6 119.3 C5 C6 H6 119.3 C8 C7 C6 120.4(2) C8 C7 H7 119.8 C6 C7 H7 119.8 C7 C8 C9 119.4(2) C7 C8 H8 120.3 C9 C8 H8 120.3 C8 C9 C10 120.65(19) C8 C9 H9 119.7 C10 C9 H9 119.7 C5 C10 C9 120.56(18) C5 C10 H10 119.7 C9 C10 H10 119.7 C13 C12 C3 110.9(2) C13 C12 C4 113.64(15) C3 C12 C4 110.11(19) C13 C12 H12 107.3 C3 C12 H12 107.3 C4 C12 H12 107.3 C14 C13 C12 112.53(17) C14 C13 H13A 109.1 C12 C13 H13A 109.1 C14 C13 H13B 109.1 C12 C13 H13B 109.1 H13A C13 H13B 107.8 C13 C14 C15 110.24(17) C13 C14 H14A 109.6 C15 C14 H14A 109.6 C13 C14 H14B 109.6 C15 C14 H14B 109.6 H14A C14 H14B 108.1 N1 C15 C16 114.54(14) N1 C15 C14 109.68(13) C16 C15 C14 110.55(15) N1 C15 H15 107.2 C16 C15 H15 107.2 C14 C15 H15 107.2 C17 C16 C21 118.86(17) C17 C16 C15 122.65(15) C21 C16 C15 118.43(15) C19 C18 C17 120.6(2) C19 C18 H18 119.7 C17 C18 H18 119.7 C18 C19 C20 119.92(19) C18 C19 H19 120.0 C20 C19 H19 120.0 C19 C20 C21 120.01(18) C19 C20 H20 120.0 C21 C20 H20 120.0 C20 C21 C16 120.33(19) C20 C21 H21 119.8 C16 C21 H21 119.8 C1 N1 C15 122.79(14) C1 N1 C4 116.78(14) C15 N1 C4 120.28(13) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C17 C16 1.386(2) C17 C18 1.393(3) C17 H17 0.9300 C1 O1 1.222(2) C1 N1 1.352(2) C1 C2 1.521(3) C2 Cl1 1.773(2) C2 H2A 0.9700 C2 H2B 0.9700 C3 C12 1.518(3) C3 H3A 0.9600 C3 H3B 0.9600 C3 H3C 0.9600 C4 N1 1.495(2) C4 C5 1.523(2) C4 C12 1.544(2) C4 H4 0.9800 C5 C6 1.384(2) C5 C10 1.392(2) C6 C7 1.381(3) C6 H6 0.9300 C7 C8 1.368(3) C7 H7 0.9300 C8 C9 1.372(3) C8 H8 0.9300 C9 C10 1.387(3) C9 H9 0.9300 C10 H10 0.9300 C12 C13 1.505(3) C12 H12 0.9800 C13 C14 1.524(3) C13 H13A 0.9700 C13 H13B 0.9700 C14 C15 1.526(3) C14 H14A 0.9700 C14 H14B 0.9700 C15 N1 1.482(2) C15 C16 1.515(2) C15 H15 0.9800 C16 C21 1.390(2) C18 C19 1.361(3) C18 H18 0.9300 C19 C20 1.384(3) C19 H19 0.9300 C20 C21 1.390(3) C20 H20 0.9300 C21 H21 0.9300 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA C17 H17 Cg1 1_555 0.93 2.98 3.879(2) 164 C21 H21 O1 2_545 0.93 2.57 3.472(3) 165 C14 H14b Cg1 2_645 0.98 2.84 3.751(2) 156 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 O1 C1 C2 Cl1 88.83(19) N1 C1 C2 Cl1 -90.01(18) N1 C4 C5 C6 -75.98(19) C12 C4 C5 C6 154.28(16) N1 C4 C5 C10 107.24(18) C12 C4 C5 C10 -22.5(2) C10 C5 C6 C7 -0.4(3) C4 C5 C6 C7 -177.46(19) C5 C6 C7 C8 -0.7(3) C6 C7 C8 C9 0.8(4) C7 C8 C9 C10 0.3(3) C6 C5 C10 C9 1.5(3) C4 C5 C10 C9 178.23(16) C8 C9 C10 C5 -1.4(3) N1 C4 C12 C13 -30.7(2) C5 C4 C12 C13 99.5(2) N1 C4 C12 C3 94.4(2) C5 C4 C12 C3 -135.4(2) C3 C12 C13 C14 -146.8(2) C4 C12 C13 C14 -22.1(3) C12 C13 C14 C15 63.8(2) C13 C14 C15 N1 -46.3(2) C13 C14 C15 C16 -173.53(16) C18 C17 C16 C21 1.3(3) C18 C17 C16 C15 -175.86(17) N1 C15 C16 C17 -41.6(2) C14 C15 C16 C17 82.9(2) N1 C15 C16 C21 141.29(16) C14 C15 C16 C21 -94.20(19) C16 C17 C18 C19 -0.4(3) C17 C18 C19 C20 -0.5(3) C18 C19 C20 C21 0.7(3) C19 C20 C21 C16 0.2(3) C17 C16 C21 C20 -1.1(3) C15 C16 C21 C20 176.11(18) O1 C1 N1 C15 177.72(17) C2 C1 N1 C15 -3.5(3) O1 C1 N1 C4 -6.8(3) C2 C1 N1 C4 171.99(14) C16 C15 N1 C1 -69.0(2) C14 C15 N1 C1 166.04(16) C16 C15 N1 C4 115.63(16) C14 C15 N1 C4 -9.3(2) C5 C4 N1 C1 101.09(17) C12 C4 N1 C1 -126.23(17) C5 C4 N1 C15 -83.27(17) C12 C4 N1 C15 49.41(19) _cod_database_fobs_code 2019808