#------------------------------------------------------------------------------ #$Date: 2020-06-05 14:28:54 +0300 (Fri, 05 Jun 2020) $ #$Revision: 252912 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/74/7157484.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_7157484 loop_ _publ_author_name 'Cui, Hao' 'Li, Ke' 'Wang, Yue' 'Song, Manman' 'Wang, Congcong' 'Wei, Donghui' 'Li, Er-Qing' 'Duan, Zheng' 'Mathey, Fran\,cois' _publ_section_title ; Copper(i)/Ganphos catalysis: enantioselective synthesis of diverse spirooxindoles using iminoesters and alkyl substituted methyleneindolinones. ; _journal_issue 19 _journal_name_full 'Organic & biomolecular chemistry' _journal_page_first 3740 _journal_page_last 3746 _journal_paper_doi 10.1039/d0ob00546k _journal_volume 18 _journal_year 2020 _chemical_absolute_configuration ad _chemical_formula_moiety 'C22 H23 Cl N2 O3' _chemical_formula_sum 'C22 H23 Cl N2 O3' _chemical_formula_weight 398.87 _space_group_crystal_system monoclinic _space_group_IT_number 5 _space_group_name_Hall 'C 2y' _space_group_name_H-M_alt 'C 1 2 1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary direct _audit_block_doi 10.5517/ccdc.csd.cc23mtn7 _audit_creation_date 2019-09-21 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2019-09-24 deposited with the CCDC. 2020-04-24 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 119.944(8) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 24.1998(14) _cell_length_b 12.3700(6) _cell_length_c 9.5879(6) _cell_measurement_reflns_used 6811 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 71.0840 _cell_measurement_theta_min 4.1430 _cell_volume 2487.0(3) _computing_cell_refinement 'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)' _computing_data_collection 'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)' _computing_data_reduction 'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXS (Sheldrick, 2008)' _diffrn_ambient_temperature 293(2) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 16.2312 _diffrn_detector_type Eos _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w -62.00 -37.00 1.00 1.50 -- -33.50 178.00 120.00 25 2 \w -47.00 -7.00 1.00 1.50 -- -33.50 -77.00 0.00 40 3 \w -85.00 -48.00 1.00 1.50 -- -33.50 -77.00 -30.00 37 4 \w -61.00 -36.00 1.00 1.50 -- -33.50 178.00-180.00 25 5 \w -105.00 -80.00 1.00 1.50 -- -33.50 178.00-180.00 25 6 \w 14.00 107.00 1.00 1.50 -- 36.47 37.00-150.00 93 7 \w 74.00 100.00 1.00 1.50 -- 36.47 178.00 -90.00 26 8 \w 51.00 106.00 1.00 1.50 -- 36.47 37.00 120.00 55 9 \w 57.00 104.00 1.00 1.50 -- 36.47 178.00 0.00 47 10 \w 68.00 102.00 1.00 1.50 -- 36.47 178.00 120.00 34 11 \w 62.00 110.00 1.00 1.50 -- 36.47 178.00 60.00 48 12 \w 61.00 96.00 1.00 7.50 -- 108.00-111.00 120.00 35 13 \w 38.00 110.00 1.00 7.50 -- 108.00 -94.00 30.00 72 14 \w 42.00 137.00 1.00 7.50 -- 108.00 -77.00-180.00 95 15 \w 39.00 127.00 1.00 7.50 -- 108.00 -30.00 60.00 88 16 \w 88.00 177.00 1.00 6.00 -- 108.00 30.00-120.00 89 17 \w 152.00 177.00 1.00 6.00 -- 108.00 45.00-120.00 25 18 \w 109.00 135.00 1.00 6.00 -- 108.00 111.00 60.00 26 19 \w 39.00 90.00 1.00 6.00 -- 108.00 -77.00 120.00 51 20 \w 27.00 56.00 1.00 1.00 -- 36.47 24.00 -78.00 29 21 \w -15.00 19.00 1.00 1.00 -- 0.00 -57.00 0.00 34 22 \w 7.00 32.00 1.00 1.00 -- 36.47 19.00 120.00 25 23 \w 54.00 80.00 1.00 1.00 -- 36.47 57.00 30.00 26 24 \w 41.00 67.00 1.00 1.00 -- 36.47 37.00 120.00 26 25 \w 57.00 82.00 1.00 1.00 -- 36.47 178.00 150.00 25 26 \w 69.00 105.00 1.00 1.00 -- 36.47 57.00 0.00 36 27 \w 76.00 105.00 1.00 1.00 -- 36.47 77.00 120.00 29 28 \w 0.00 31.00 1.00 1.00 -- 36.47 91.00 -2.60 31 29 \w 66.00 92.00 1.00 1.00 -- 36.47 19.00 120.00 26 30 \w 35.00 61.00 1.00 1.00 -- 36.47 57.00 150.00 26 31 \w 32.00 63.00 1.00 1.00 -- 36.47 77.00 60.00 31 32 \w 42.00 100.00 1.00 1.00 -- 36.47 77.00 30.00 58 33 \w -9.00 16.00 1.00 1.00 -- 36.47 108.00 58.07 25 34 \w 35.00 61.00 1.00 1.00 -- 36.47 57.00 0.00 26 35 \w 9.00 34.00 1.00 1.00 -- 36.47 77.00 30.00 25 36 \w 24.00 50.00 1.00 1.00 -- 36.47 57.00 120.00 26 37 \w 84.00 110.00 1.00 1.00 -- 36.47 178.00 90.00 26 38 \w 14.00 40.00 1.00 1.00 -- 36.47 77.00 120.00 26 39 \w 45.00 71.00 1.00 1.00 -- 36.47 57.00 -30.00 26 40 \w 19.00 44.00 1.00 1.00 -- 36.47 57.00-180.00 25 41 \w 58.00 84.00 1.00 1.00 -- 36.47 178.00-120.00 26 42 \w 130.00 156.00 1.00 6.00 -- 108.00 30.00 120.00 26 43 \w 87.00 143.00 1.00 6.00 -- 108.00 30.00 60.00 56 44 \w 88.00 114.00 1.00 6.00 -- 108.00 61.00 0.00 26 45 \w 88.00 114.00 1.00 6.00 -- 108.00 61.00 -30.00 26 46 \w 79.00 104.00 1.00 6.00 -- 108.00 77.00 -60.00 25 47 \w 83.00 109.00 1.00 6.00 -- 108.00 77.00 90.00 26 48 \w 86.00 112.00 1.00 6.00 -- 108.00 30.00 120.00 26 49 \w 89.00 115.00 1.00 6.00 -- 108.00 61.00 60.00 26 50 \w 79.00 104.00 1.00 6.00 -- 108.00 77.00 60.00 25 51 \w 153.00 178.00 1.00 6.00 -- 108.00 30.00 -30.00 25 52 \w 79.00 104.00 1.00 6.00 -- 108.00 77.00 0.00 25 53 \w 88.00 114.00 1.00 6.00 -- 108.00 45.00 90.00 26 54 \w 88.00 118.00 1.00 6.00 -- 108.00 61.00 30.00 30 55 \w 81.00 106.00 1.00 6.00 -- 108.00 74.00 28.64 25 56 \w 88.00 114.00 1.00 6.00 -- 108.00 61.00 90.00 26 57 \w 129.00 155.00 1.00 6.00 -- 108.00 77.00 -30.00 26 58 \w 82.00 133.00 1.00 6.00 -- 108.00 30.00 30.00 51 59 \w 79.00 104.00 1.00 6.00 -- 108.00 77.00 -30.00 25 60 \w 84.00 123.00 1.00 6.00 -- 108.00 30.00 0.00 39 61 \w 88.00 124.00 1.00 6.00 -- 108.00 45.00 0.00 36 62 \w 87.00 117.00 1.00 6.00 -- 108.00 42.00 -9.89 30 63 \w 88.00 114.00 1.00 6.00 -- 108.00 61.00 -60.00 26 64 \w 79.00 105.00 1.00 6.00 -- 108.00 77.00 30.00 26 65 \w 89.00 137.00 1.00 6.00 -- 108.00 45.00 -30.00 48 66 \w 89.00 132.00 1.00 6.00 -- 108.00 45.00 30.00 43 67 \w 79.00 105.00 1.00 6.00 -- 108.00 77.00 5.88 26 68 \w 83.00 129.00 1.00 6.00 -- 108.00 30.00 -30.00 46 69 \w 83.00 129.00 1.00 6.00 -- 108.00 30.00 90.00 46 70 \w 24.00 50.00 1.00 1.00 -- 36.47 57.00 120.00 26 71 \w 51.00 77.00 1.00 1.00 -- 36.47 57.00 0.00 26 72 \w 41.00 67.00 1.00 1.00 -- 36.47 37.00 120.00 26 73 \w 69.00 95.00 1.00 1.00 -- 36.47 57.00 30.00 26 74 \w 24.00 50.00 1.00 1.00 -- 36.47 57.00-180.00 26 75 \w 84.00 110.00 1.00 6.00 -- 108.00 30.00 0.00 26 76 \w 89.00 115.00 1.00 6.00 -- 108.00 45.00 -30.00 26 77 \w 91.00 117.00 1.00 6.00 -- 108.00 61.00 60.00 26 78 \w 87.00 113.00 1.00 6.00 -- 108.00 42.00 110.61 26 79 \w 85.00 111.00 1.00 6.00 -- 108.00 37.00 115.89 26 80 \w 69.00 95.00 1.00 1.00 -- 36.47 57.00 30.00 26 81 \w 41.00 67.00 1.00 1.00 -- 36.47 37.00 120.00 26 82 \w 24.00 50.00 1.00 1.00 -- 36.47 57.00-180.00 26 83 \w 51.00 77.00 1.00 1.00 -- 36.47 57.00 0.00 26 84 \w 24.00 50.00 1.00 1.00 -- 36.47 57.00 120.00 26 85 \w 91.00 117.00 1.00 6.00 -- 108.00 61.00 60.00 26 86 \w 89.00 115.00 1.00 6.00 -- 108.00 45.00 -30.00 26 87 \w 84.00 110.00 1.00 6.00 -- 108.00 30.00 0.00 26 88 \w 24.00 50.00 1.00 1.00 -- 36.47 57.00 120.00 26 89 \w 69.00 95.00 1.00 1.00 -- 36.47 57.00 30.00 26 90 \w 24.00 50.00 1.00 1.00 -- 36.47 57.00-180.00 26 91 \w 41.00 67.00 1.00 1.00 -- 36.47 37.00 120.00 26 92 \w 51.00 77.00 1.00 1.00 -- 36.47 57.00 0.00 26 93 \w 84.00 110.00 1.00 6.00 -- 108.00 30.00 0.00 26 94 \w 89.00 115.00 1.00 6.00 -- 108.00 45.00 -30.00 26 95 \w 91.00 117.00 1.00 6.00 -- 108.00 61.00 60.00 26 96 \w 86.00 112.00 1.00 6.00 -- 108.00 39.00 82.69 26 97 \w 69.00 95.00 1.00 1.00 -- 36.47 57.00 30.00 26 98 \w 41.00 67.00 1.00 1.00 -- 36.47 37.00 120.00 26 99 \w 24.00 50.00 1.00 1.00 -- 36.47 57.00-180.00 26 100 \w 51.00 77.00 1.00 1.00 -- 36.47 57.00 0.00 26 101 \w 24.00 50.00 1.00 1.00 -- 36.47 57.00 120.00 26 102 \w 91.00 117.00 1.00 6.00 -- 108.00 61.00 60.00 26 103 \w 89.00 115.00 1.00 6.00 -- 108.00 45.00 -30.00 26 104 \w 84.00 110.00 1.00 6.00 -- 108.00 30.00 0.00 26 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0401215000 _diffrn_orient_matrix_UB_12 0.0387657000 _diffrn_orient_matrix_UB_13 -0.1755796000 _diffrn_orient_matrix_UB_21 -0.0589977000 _diffrn_orient_matrix_UB_22 0.0085798000 _diffrn_orient_matrix_UB_23 0.0207410000 _diffrn_orient_matrix_UB_31 0.0174342000 _diffrn_orient_matrix_UB_32 0.1180243000 _diffrn_orient_matrix_UB_33 0.0561157000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0281 _diffrn_reflns_av_unetI/netI 0.0257 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 17070 _diffrn_reflns_point_group_measured_fraction_full 0.924 _diffrn_reflns_point_group_measured_fraction_max 0.924 _diffrn_reflns_theta_full 67.063 _diffrn_reflns_theta_max 67.063 _diffrn_reflns_theta_min 4.217 _diffrn_source 'fine-focus sealed X-ray tube' _diffrn_source_type 'Enhance (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 1.526 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.83221 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.065 _exptl_crystal_description prism _exptl_crystal_F_000 840 _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.09 _refine_diff_density_max 0.251 _refine_diff_density_min -0.201 _refine_diff_density_rms 0.034 _refine_ls_abs_structure_details ; Flack x determined using 1510 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.000(18) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 264 _refine_ls_number_reflns 4120 _refine_ls_number_restraints 3 _refine_ls_restrained_S_all 1.051 _refine_ls_R_factor_all 0.0472 _refine_ls_R_factor_gt 0.0448 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0880P)^2^+0.1735P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1259 _refine_ls_wR_factor_ref 0.1291 _reflns_Friedel_coverage 0.761 _reflns_Friedel_fraction_full 0.842 _reflns_Friedel_fraction_max 0.842 _reflns_number_gt 3851 _reflns_number_total 4120 _reflns_threshold_expression 'I > 2\s(I)' _iucr_refine_instructions_details ; 201909229.res created by SHELXL-2014/7 TITL 201909229 in C2 #5 REM reset to C6 #5 CELL 1.54184 24.199774 12.369973 9.587878 90 119.9441 90 ZERR 4 0.001353 0.000587 0.000575 0 0.0078 0 LATT -7 SYMM -X,+Y,-Z SFAC C H Cl N O UNIT 88 92 4 8 12 EQIV $1 0.5-X,0.5+Y,1-Z DFIX 0.87 N2 H2 DFIX 0.87 N1 H1a L.S. 24 0 0 PLAN 20 SIZE 0.09 0.12 0.17 HTAB N1 N2_$1 MPLA C1 C2 C3 C4 C5 C6 MPLA C8 C9 C10 C11 C12 C13 C14 C15 N1 BOND $h ABIN conf fmap 2 acta OMIT 1 1 0 OMIT 1 -1 0 REM REM REM WGHT 0.088000 0.173500 FVAR 5.56296 C1 1 0.130476 0.323533 0.376817 11.00000 0.05620 0.05151 = 0.06521 0.00803 0.03176 0.00460 AFIX 43 H1 2 0.125837 0.327719 0.274659 11.00000 -1.20000 AFIX 0 C2 1 0.088199 0.376094 0.411658 11.00000 0.04687 0.05082 = 0.09485 0.00597 0.03390 0.00439 C3 1 0.094033 0.375179 0.560829 11.00000 0.06387 0.07936 = 0.10138 -0.01124 0.05180 0.00131 AFIX 43 H3 2 0.065344 0.412474 0.580866 11.00000 -1.20000 AFIX 0 C4 1 0.143157 0.317979 0.679539 11.00000 0.07558 0.12601 = 0.07226 -0.01376 0.04633 0.00085 AFIX 43 H4 2 0.148192 0.316085 0.782222 11.00000 -1.20000 AFIX 0 C5 1 0.185768 0.262481 0.648416 11.00000 0.06218 0.07848 = 0.06320 0.00400 0.03294 0.00618 AFIX 43 H5 2 0.218811 0.223304 0.730432 11.00000 -1.20000 AFIX 0 C6 1 0.179761 0.264669 0.497753 11.00000 0.04640 0.04041 = 0.05635 -0.00115 0.02677 -0.00634 C7 1 0.227517 0.202752 0.470949 11.00000 0.05135 0.03553 = 0.04517 0.00702 0.02230 0.00288 AFIX 13 H7 2 0.240168 0.140312 0.543387 11.00000 -1.20000 AFIX 0 C8 1 0.291801 0.265022 0.515425 11.00000 0.04553 0.03768 = 0.04420 0.00332 0.02235 0.00291 C9 1 0.283571 0.387664 0.504622 11.00000 0.05278 0.04006 = 0.05176 0.00478 0.02811 0.00202 C10 1 0.340500 0.248481 0.689978 11.00000 0.04278 0.04953 = 0.04531 0.00644 0.02310 0.00592 C11 1 0.355873 0.348382 0.765960 11.00000 0.04706 0.05745 = 0.05266 -0.00202 0.02458 0.00115 C12 1 0.399053 0.357943 0.928738 11.00000 0.06820 0.08984 = 0.05398 -0.01440 0.02305 -0.01731 AFIX 43 H12 2 0.409014 0.425156 0.978894 11.00000 -1.20000 AFIX 0 C13 1 0.426759 0.265344 1.014032 11.00000 0.06048 0.12532 = 0.04333 0.00798 0.01276 -0.00337 AFIX 43 H13 2 0.456636 0.270499 1.123050 11.00000 -1.20000 AFIX 0 C14 1 0.411479 0.165040 0.942428 11.00000 0.06242 0.10527 = 0.05662 0.03111 0.02498 0.02307 AFIX 43 H14 2 0.430562 0.103489 1.003352 11.00000 -1.20000 AFIX 0 C15 1 0.367532 0.155582 0.779057 11.00000 0.06092 0.05833 = 0.05924 0.01595 0.03138 0.01529 AFIX 43 H15 2 0.356463 0.087943 0.730368 11.00000 -1.20000 AFIX 0 C16 1 0.306899 0.224185 0.382749 11.00000 0.06097 0.04395 = 0.04807 0.00772 0.03146 0.00532 AFIX 13 H16 2 0.293674 0.281737 0.302077 11.00000 -1.20000 AFIX 0 C17 1 0.260486 0.130005 0.302922 11.00000 0.06734 0.03985 = 0.04787 0.00214 0.02944 0.00700 AFIX 13 H17 2 0.279020 0.063311 0.363692 11.00000 -1.20000 AFIX 0 C18 1 0.377618 0.200930 0.441218 11.00000 0.06990 0.07126 = 0.07127 0.00869 0.04926 0.00808 AFIX 13 H18 2 0.393065 0.147967 0.528774 11.00000 -1.20000 AFIX 0 C19 1 0.417354 0.304351 0.506110 11.00000 0.06895 0.10273 = 0.09834 -0.01179 0.05330 -0.01646 AFIX 137 H19A 2 0.399071 0.360412 0.426552 11.00000 -1.50000 H19B 2 0.460264 0.290566 0.530145 11.00000 -1.50000 H19C 2 0.417605 0.326825 0.602260 11.00000 -1.50000 AFIX 0 C20 1 0.386050 0.153401 0.305149 11.00000 0.09977 0.08929 = 0.10380 -0.00181 0.07574 0.00906 AFIX 137 H20A 2 0.366293 0.083465 0.276126 11.00000 -1.50000 H20B 2 0.430683 0.146601 0.340904 11.00000 -1.50000 H20C 2 0.366448 0.200404 0.213297 11.00000 -1.50000 AFIX 0 C21 1 0.240980 0.113003 0.126572 11.00000 0.08408 0.06498 = 0.05226 -0.00415 0.03310 0.00686 C22 1 0.230832 -0.013667 -0.066979 11.00000 0.27081 0.12301 = 0.08362 -0.03568 0.07442 0.04081 AFIX 137 H22A 2 0.187988 0.009544 -0.139621 11.00000 -1.50000 H22B 2 0.234199 -0.090057 -0.078793 11.00000 -1.50000 H22C 2 0.259746 0.023930 -0.091159 11.00000 -1.50000 AFIX 0 CL1 3 0.024960 0.449435 0.258498 11.00000 0.07024 0.10069 = 0.13368 0.03601 0.04659 0.03419 N1 4 0.322143 0.429501 0.653890 11.00000 0.05997 0.03909 = 0.06107 -0.00629 0.02731 -0.00159 H1A 2 0.323002 0.495263 0.674723 11.00000 0.04956 N2 4 0.203001 0.158461 0.309379 11.00000 0.05691 0.03639 = 0.04944 0.00190 0.02159 0.00275 H2 2 0.182437 0.206530 0.241244 11.00000 0.04869 O1 5 0.249396 0.439535 0.383486 11.00000 0.06572 0.04005 = 0.06494 0.01180 0.02705 0.00711 O2 5 0.220507 0.181865 0.028032 11.00000 0.14847 0.09148 = 0.05191 0.00714 0.04126 0.02458 O3 5 0.246823 0.009925 0.097499 11.00000 0.15393 0.06611 = 0.07346 -0.01965 0.05425 0.01310 HKLF 4 REM 201909229 in C2 #5 REM R1 = 0.0448 for 3851 Fo > 4sig(Fo) and 0.0472 for all 4120 data REM 264 parameters refined using 3 restraints END WGHT 0.0881 0.1735 REM Highest difference peak 0.251, deepest hole -0.201, 1-sigma level 0.034 Q1 1 0.0023 0.3822 0.2203 11.00000 0.05 0.25 Q2 1 0.0308 0.4385 0.1784 11.00000 0.05 0.13 Q3 1 0.4075 0.2820 0.9418 11.00000 0.05 0.12 Q4 1 0.0190 0.5359 0.2389 11.00000 0.05 0.12 Q5 1 0.1920 0.1531 0.0402 11.00000 0.05 0.12 Q6 1 0.2437 0.1969 0.0934 11.00000 0.05 0.12 Q7 1 0.4557 0.0164 0.3280 11.00000 0.05 0.11 Q8 1 0.2614 0.2481 0.4925 11.00000 0.05 0.11 Q9 1 0.5110 0.1575 1.1199 11.00000 0.05 0.11 Q10 1 0.0317 0.5075 0.6347 11.00000 0.05 0.11 Q11 1 0.2776 0.2207 0.3049 11.00000 0.05 0.11 Q12 1 0.3908 0.0714 0.2922 11.00000 0.05 0.10 Q13 1 0.3505 0.2503 0.7612 11.00000 0.05 0.10 Q14 1 0.2217 0.2660 0.5061 11.00000 0.05 0.10 Q15 1 0.4706 0.1286 0.6016 11.00000 0.05 0.10 Q16 1 0.3391 0.2089 0.7381 11.00000 0.05 0.09 Q17 1 0.2572 -0.0589 0.1284 11.00000 0.05 0.09 Q18 1 0.3466 0.0034 0.8982 11.00000 0.05 0.09 Q19 1 0.3236 0.2095 0.0382 11.00000 0.05 0.09 Q20 1 0.3912 0.2933 0.4270 11.00000 0.05 0.09 REM The information below was added by Olex2. REM REM R1 = 0.0448 for 3851 Fo > 4sig(Fo) and 0.0472 for all 17073 data REM n/a parameters refined using n/a restraints REM Highest difference peak 0.25, deepest hole -0.20 REM Mean Shift 0, Max Shift -0.002. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = 0.0472 REM R1_gt = 0.0448 REM wR_ref = 0.1291 REM GOOF = 1.051 REM Shift_max = -0.002 REM Shift_mean = 0 REM Reflections_all = 17073 REM Reflections_gt = 3851 REM Parameters = n/a REM Hole = -0.20 REM Peak = 0.25 REM Flack = 0.000(18) ; _cod_data_source_file d0ob00546k2.cif _cod_data_source_block 201909229 _cod_depositor_comments 'Adding full bibliography for 7157484.cif.' _cod_database_code 7157484 _shelx_shelxl_version_number 2014/7 _chemical_oxdiff_formula C20H20O4Cl1 _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_max 0.875 _shelx_estimated_absorpt_t_min 0.781 _reflns_odcompleteness_completeness 99.96 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups At 1.5 times of: All C(H,H,H) groups 2. Restrained distances N2-H2 0.87 with sigma of 0.02 N1-H1A 0.87 with sigma of 0.02 3.a Ternary CH refined with riding coordinates: C7(H7), C16(H16), C17(H17), C18(H18) 3.b Aromatic/amide H refined with riding coordinates: C1(H1), C3(H3), C4(H4), C5(H5), C12(H12), C13(H13), C14(H14), C15(H15) 3.c Idealised Me refined as rotating group: C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C22(H22A,H22B,H22C) ; _shelx_fab_file ; -28 0 4 0.1068 0.1205 -28 0 5 0.1169 0.1118 -28 0 6 0.1801 -0.0982 -28 0 7 -0.0300 -0.0689 -28 0 8 -0.1588 0.0358 -28 2 4 0.0823 0.6282 -28 2 5 0.1800 0.3092 -28 2 6 0.3016 0.1313 -28 2 7 -0.0882 0.0073 -27 1 2 0.4666 -0.0931 -27 1 3 0.4393 0.0701 -27 1 4 0.4371 0.4544 -27 1 5 0.0874 0.1265 -27 1 6 0.2912 -0.2586 -27 1 7 -0.1346 -0.1389 -27 1 8 -0.4162 -0.2515 -27 3 3 -0.1081 -0.0917 -27 3 4 -0.3957 0.7139 -27 3 5 -0.1317 0.4306 -27 3 6 -0.2275 0.2718 -27 3 7 -0.7251 0.1103 -27 3 8 -0.1765 -0.1534 -27 5 5 0.1056 0.1096 -27 5 6 0.0008 0.1423 -26 0 1 -0.9936 0.0994 -26 0 2 0.2190 -0.1671 -26 0 3 0.2352 -0.1093 -26 0 4 0.2926 0.1790 -26 0 5 -0.1906 0.1300 -26 0 6 0.1508 -0.1713 -26 0 7 -0.2069 -0.0912 -26 0 8 -0.8136 0.0811 -26 0 9 0.0496 0.0288 -26 2 2 -0.1696 0.0074 -26 2 3 -0.1587 0.1029 -26 2 4 0.2021 0.9812 -26 2 5 0.0951 0.4771 -26 2 6 0.5598 0.0868 -26 2 7 0.1100 0.4757 -26 2 8 0.1382 -0.0329 -26 2 9 0.3129 0.0843 -26 4 2 -0.1299 -0.3974 -26 4 3 -0.1107 -0.5241 -26 4 4 -0.2771 -0.2903 -26 4 5 -0.1305 -0.0534 -26 4 6 -0.1813 -0.4805 -26 4 7 -0.3718 -0.3861 -26 4 8 0.2186 -0.5263 -26 6 4 -0.1344 0.3153 -26 6 5 -0.2638 0.2508 -26 6 6 -0.1098 0.0329 -25 1 1 -0.7867 -0.2465 -25 1 2 0.2990 -0.2750 -25 1 3 0.2078 -0.2007 -25 1 4 0.4701 0.2591 -25 1 5 -0.0922 0.2201 -25 1 6 0.5595 -0.5086 -25 1 7 0.1420 -0.2238 -25 1 8 -0.4351 -0.4153 -25 1 9 0.2270 -0.0869 -25 3 1 -0.0509 -0.4282 -25 3 2 -0.6484 -0.4119 -25 3 3 -0.5206 -0.5640 -25 3 4 -0.1804 0.4043 -25 3 5 -0.1972 0.5737 -25 3 6 -0.0704 -0.0154 -25 3 7 -0.7822 0.2964 -25 3 8 -0.4891 0.0446 -25 3 9 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0.1382 0.0329 26 -2 -7 0.1100 -0.4757 26 -2 -6 0.5598 -0.0868 26 -2 -5 0.0951 -0.4771 26 -2 -4 0.2021 -0.9812 26 -2 -3 -0.1587 -0.1029 26 -2 -2 -0.1696 -0.0074 27 -5 -6 0.0008 -0.1423 27 -5 -5 0.1056 -0.1096 27 -3 -8 -0.1765 0.1534 27 -3 -7 -0.7251 -0.1103 27 -3 -6 -0.2275 -0.2718 27 -3 -5 -0.1317 -0.4306 27 -3 -4 -0.3957 -0.7139 27 -3 -3 -0.1081 0.0917 27 -1 -8 -0.4162 0.2515 27 -1 -7 -0.1346 0.1389 27 -1 -6 0.2912 0.2586 27 -1 -5 0.0874 -0.1265 27 -1 -4 0.4371 -0.4544 27 -1 -3 0.4393 -0.0701 27 -1 -2 0.4666 0.0931 28 -2 -7 -0.0882 -0.0073 28 -2 -6 0.3016 -0.1313 28 -2 -5 0.1800 -0.3092 28 -2 -4 0.0823 -0.6282 0 0 0 0.0 0.0 ; _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _oxdiff_exptl_absorpt_empirical_full_max 1.321 _oxdiff_exptl_absorpt_empirical_full_min 0.882 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -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 C1 C 0.13048(15) 0.3235(3) 0.3768(4) 0.0570(7) Uani 1 1 d . . . . . H1 H 0.1258 0.3277 0.2747 0.068 Uiso 1 1 calc R . . . . C2 C 0.08820(15) 0.3761(3) 0.4117(5) 0.0648(8) Uani 1 1 d . . . . . C3 C 0.09403(18) 0.3752(4) 0.5608(5) 0.0769(10) Uani 1 1 d . . . . . H3 H 0.0653 0.4125 0.5809 0.092 Uiso 1 1 calc R . . . . C4 C 0.1432(2) 0.3180(5) 0.6795(5) 0.0871(13) Uani 1 1 d . . . . . H4 H 0.1482 0.3161 0.7822 0.105 Uiso 1 1 calc R . . . . C5 C 0.18577(17) 0.2625(4) 0.6484(4) 0.0672(8) Uani 1 1 d . . . . . H5 H 0.2188 0.2233 0.7304 0.081 Uiso 1 1 calc R . . . . C6 C 0.17976(12) 0.2647(2) 0.4978(3) 0.0472(6) Uani 1 1 d . . . . . C7 C 0.22752(13) 0.2028(2) 0.4709(3) 0.0448(6) Uani 1 1 d . . . . . H7 H 0.2402 0.1403 0.5434 0.054 Uiso 1 1 calc R . . . . C8 C 0.29180(12) 0.2650(2) 0.5154(3) 0.0425(5) Uani 1 1 d . . . . . C9 C 0.28357(13) 0.3877(3) 0.5046(3) 0.0473(6) Uani 1 1 d . . . . . C10 C 0.34050(12) 0.2485(2) 0.6900(3) 0.0454(6) Uani 1 1 d . . . . . C11 C 0.35587(13) 0.3484(3) 0.7660(3) 0.0525(7) Uani 1 1 d . . . . . C12 C 0.39905(19) 0.3579(4) 0.9287(4) 0.0740(10) Uani 1 1 d . . . . . H12 H 0.4090 0.4252 0.9789 0.089 Uiso 1 1 calc R . . . . C13 C 0.42676(18) 0.2653(5) 1.0140(4) 0.0822(12) Uani 1 1 d . . . . . H13 H 0.4566 0.2705 1.1230 0.099 Uiso 1 1 calc R . . . . C14 C 0.41148(17) 0.1650(4) 0.9424(4) 0.0769(11) Uani 1 1 d . . . . . H14 H 0.4306 0.1035 1.0034 0.092 Uiso 1 1 calc R . . . . C15 C 0.36753(15) 0.1556(3) 0.7791(4) 0.0589(8) Uani 1 1 d . . . . . H15 H 0.3565 0.0879 0.7304 0.071 Uiso 1 1 calc R . . . . C16 C 0.30690(14) 0.2242(2) 0.3827(3) 0.0491(6) Uani 1 1 d . . . . . H16 H 0.2937 0.2817 0.3021 0.059 Uiso 1 1 calc R . . . . C17 C 0.26049(15) 0.1300(3) 0.3029(3) 0.0514(6) Uani 1 1 d . . . . . H17 H 0.2790 0.0633 0.3637 0.062 Uiso 1 1 calc R . . . . C18 C 0.37762(18) 0.2009(3) 0.4412(4) 0.0646(8) Uani 1 1 d . . . . . H18 H 0.3931 0.1480 0.5288 0.078 Uiso 1 1 calc R . . . . C19 C 0.41735(19) 0.3044(4) 0.5061(6) 0.0849(12) Uani 1 1 d . . . . . H19A H 0.3991 0.3604 0.4266 0.127 Uiso 1 1 calc GR . . . . H19B H 0.4603 0.2906 0.5301 0.127 Uiso 1 1 calc GR . . . . H19C H 0.4176 0.3268 0.6023 0.127 Uiso 1 1 calc GR . . . . C20 C 0.3861(2) 0.1534(4) 0.3051(6) 0.0866(12) Uani 1 1 d . . . . . H20A H 0.3663 0.0835 0.2761 0.130 Uiso 1 1 calc GR . . . . H20B H 0.4307 0.1466 0.3409 0.130 Uiso 1 1 calc GR . . . . H20C H 0.3664 0.2004 0.2133 0.130 Uiso 1 1 calc GR . . . . C21 C 0.24098(19) 0.1130(3) 0.1266(4) 0.0675(9) Uani 1 1 d . . . . . C22 C 0.2308(5) -0.0137(7) -0.0670(7) 0.165(4) Uani 1 1 d . . . . . H22A H 0.1880 0.0095 -0.1396 0.248 Uiso 1 1 calc GR . . . . H22B H 0.2342 -0.0901 -0.0788 0.248 Uiso 1 1 calc GR . . . . H22C H 0.2597 0.0239 -0.0912 0.248 Uiso 1 1 calc GR . . . . Cl1 Cl 0.02496(5) 0.44943(12) 0.25850(18) 0.1034(5) Uani 1 1 d . . . . . N1 N 0.32214(13) 0.4295(2) 0.6539(3) 0.0547(6) Uani 1 1 d D . . . . H1A H 0.3230(16) 0.495(2) 0.675(4) 0.050(9) Uiso 1 1 d D . . . . N2 N 0.20300(12) 0.1585(2) 0.3094(3) 0.0498(5) Uani 1 1 d D . . . . H2 H 0.1824(15) 0.207(2) 0.241(4) 0.049(8) Uiso 1 1 d D . . . . O1 O 0.24940(11) 0.43953(19) 0.3835(3) 0.0594(5) Uani 1 1 d . . . . . O2 O 0.2205(2) 0.1819(3) 0.0280(3) 0.1012(11) Uani 1 1 d . . . . . O3 O 0.2468(2) 0.0099(3) 0.0975(4) 0.0989(11) 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 C1 0.0562(16) 0.0515(18) 0.0652(16) 0.0080(13) 0.0318(14) 0.0046(13) C2 0.0469(15) 0.0508(19) 0.095(2) 0.0060(16) 0.0339(15) 0.0044(13) C3 0.0639(19) 0.079(3) 0.101(3) -0.011(2) 0.052(2) 0.0013(18) C4 0.076(2) 0.126(4) 0.072(2) -0.014(2) 0.0463(19) 0.001(2) C5 0.0622(18) 0.078(3) 0.0632(17) 0.0040(16) 0.0329(15) 0.0062(17) C6 0.0464(13) 0.0404(15) 0.0563(14) -0.0011(11) 0.0268(11) -0.0063(11) C7 0.0514(13) 0.0355(14) 0.0452(12) 0.0070(10) 0.0223(11) 0.0029(10) C8 0.0455(12) 0.0377(15) 0.0442(12) 0.0033(10) 0.0223(10) 0.0029(10) C9 0.0528(14) 0.0401(15) 0.0518(14) 0.0048(11) 0.0281(12) 0.0020(11) C10 0.0428(12) 0.0495(17) 0.0453(12) 0.0064(11) 0.0231(10) 0.0059(11) C11 0.0471(14) 0.057(2) 0.0527(14) -0.0020(12) 0.0246(12) 0.0012(12) C12 0.068(2) 0.090(3) 0.0540(17) -0.0144(17) 0.0230(15) -0.0173(19) C13 0.0605(19) 0.125(4) 0.0433(15) 0.008(2) 0.0128(14) -0.003(2) C14 0.0624(18) 0.105(3) 0.0566(18) 0.031(2) 0.0250(15) 0.023(2) C15 0.0609(16) 0.058(2) 0.0592(15) 0.0160(14) 0.0314(14) 0.0153(14) C16 0.0610(16) 0.0440(16) 0.0481(13) 0.0077(10) 0.0315(12) 0.0053(12) C17 0.0673(16) 0.0398(16) 0.0479(13) 0.0021(11) 0.0294(12) 0.0070(12) C18 0.0699(19) 0.071(2) 0.0713(19) 0.0087(16) 0.0493(17) 0.0081(16) C19 0.069(2) 0.103(4) 0.098(3) -0.012(2) 0.053(2) -0.016(2) C20 0.100(3) 0.089(3) 0.104(3) -0.002(2) 0.076(3) 0.009(2) C21 0.084(2) 0.065(2) 0.0523(17) -0.0041(15) 0.0331(16) 0.0069(18) C22 0.271(10) 0.123(6) 0.084(4) -0.036(4) 0.074(5) 0.041(7) Cl1 0.0702(6) 0.1007(9) 0.1337(10) 0.0360(7) 0.0466(6) 0.0342(6) N1 0.0600(13) 0.0391(15) 0.0611(13) -0.0063(11) 0.0273(11) -0.0016(11) N2 0.0569(13) 0.0364(13) 0.0494(11) 0.0019(9) 0.0216(10) 0.0028(10) O1 0.0657(12) 0.0400(12) 0.0649(12) 0.0118(9) 0.0271(10) 0.0071(10) O2 0.148(3) 0.091(2) 0.0519(13) 0.0071(14) 0.0413(16) 0.025(2) O3 0.154(3) 0.0661(19) 0.0735(17) -0.0197(13) 0.0542(18) 0.0131(19) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 '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 C2 C1 H1 120.8 . . ? C6 C1 H1 120.8 . . ? C6 C1 C2 118.4(3) . . ? C1 C2 Cl1 118.8(3) . . ? C3 C2 C1 123.1(3) . . ? C3 C2 Cl1 118.2(3) . . ? C2 C3 H3 121.0 . . ? C4 C3 C2 118.0(3) . . ? C4 C3 H3 121.0 . . ? C3 C4 H4 119.7 . . ? C3 C4 C5 120.6(4) . . ? C5 C4 H4 119.7 . . ? C4 C5 H5 119.5 . . ? C6 C5 C4 120.9(4) . . ? C6 C5 H5 119.5 . . ? C1 C6 C7 122.4(2) . . ? C5 C6 C1 119.0(3) . . ? C5 C6 C7 118.6(3) . . ? C6 C7 H7 105.9 . . ? C6 C7 C8 115.9(2) . . ? C8 C7 H7 105.9 . . ? N2 C7 C6 115.5(2) . . ? N2 C7 H7 105.9 . . ? N2 C7 C8 106.9(2) . . ? C9 C8 C7 112.7(2) . . ? C9 C8 C16 109.8(2) . . ? C10 C8 C7 110.5(2) . . ? C10 C8 C9 102.3(2) . . ? C10 C8 C16 119.2(2) . . ? C16 C8 C7 102.6(2) . . ? N1 C9 C8 108.0(2) . . ? O1 C9 C8 126.2(3) . . ? O1 C9 N1 125.8(3) . . ? C11 C10 C8 108.6(2) . . ? C15 C10 C8 131.7(3) . . ? C15 C10 C11 119.6(3) . . ? C10 C11 N1 109.6(2) . . ? C12 C11 C10 121.5(3) . . ? C12 C11 N1 128.9(3) . . ? C11 C12 H12 121.0 . . ? C13 C12 C11 118.0(4) . . ? C13 C12 H12 121.0 . . ? C12 C13 H13 119.1 . . ? C12 C13 C14 121.7(3) . . ? C14 C13 H13 119.1 . . ? C13 C14 H14 119.9 . . ? C13 C14 C15 120.1(4) . . ? C15 C14 H14 119.9 . . ? C10 C15 C14 119.0(4) . . ? C10 C15 H15 120.5 . . ? C14 C15 H15 120.5 . . ? C8 C16 H16 106.8 . . ? C17 C16 C8 103.9(2) . . ? C17 C16 H16 106.8 . . ? C17 C16 C18 116.4(3) . . ? C18 C16 C8 115.5(2) . . ? C18 C16 H16 106.8 . . ? C16 C17 H17 109.8 . . ? C21 C17 C16 113.7(3) . . ? C21 C17 H17 109.8 . . ? N2 C17 C16 105.7(2) . . ? N2 C17 H17 109.8 . . ? N2 C17 C21 107.7(3) . . ? C16 C18 H18 108.4 . . ? C19 C18 C16 110.5(3) . . ? C19 C18 H18 108.4 . . ? C19 C18 C20 110.0(3) . . ? C20 C18 C16 110.9(3) . . ? C20 C18 H18 108.4 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19B 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C18 C20 H20A 109.5 . . ? C18 C20 H20B 109.5 . . ? C18 C20 H20C 109.5 . . ? H20A C20 H20B 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? O2 C21 C17 124.1(4) . . ? O2 C21 O3 124.8(3) . . ? O3 C21 C17 111.0(3) . . ? H22A C22 H22B 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? O3 C22 H22A 109.5 . . ? O3 C22 H22B 109.5 . . ? O3 C22 H22C 109.5 . . ? C9 N1 C11 111.5(3) . . ? C9 N1 H1A 123(2) . . ? C11 N1 H1A 125(2) . . ? C7 N2 C17 104.1(2) . . ? C7 N2 H2 109(2) . . ? C17 N2 H2 110(2) . . ? C21 O3 C22 115.0(4) . . ? 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 C1 H1 0.9300 . ? C1 C2 1.386(5) . ? C1 C6 1.384(4) . ? C2 C3 1.365(6) . ? C2 Cl1 1.754(4) . ? C3 H3 0.9300 . ? C3 C4 1.363(7) . ? C4 H4 0.9300 . ? C4 C5 1.390(6) . ? C5 H5 0.9300 . ? C5 C6 1.378(4) . ? C6 C7 1.512(4) . ? C7 H7 0.9800 . ? C7 C8 1.592(4) . ? C7 N2 1.461(4) . ? C8 C9 1.527(4) . ? C8 C10 1.504(4) . ? C8 C16 1.572(3) . ? C9 N1 1.362(4) . ? C9 O1 1.219(4) . ? C10 C11 1.388(4) . ? C10 C15 1.386(4) . ? C11 C12 1.383(4) . ? C11 N1 1.397(4) . ? C12 H12 0.9300 . ? C12 C13 1.372(7) . ? C13 H13 0.9300 . ? C13 C14 1.376(7) . ? C14 H14 0.9300 . ? C14 C15 1.391(5) . ? C15 H15 0.9300 . ? C16 H16 0.9800 . ? C16 C17 1.532(4) . ? C16 C18 1.539(4) . ? C17 H17 0.9800 . ? C17 C21 1.526(4) . ? C17 N2 1.466(4) . ? C18 H18 0.9800 . ? C18 C19 1.533(6) . ? C18 C20 1.535(5) . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 O2 1.182(5) . ? C21 O3 1.328(5) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C22 O3 1.453(6) . ? N1 H1A 0.84(2) . ? N2 H2 0.84(2) . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A N2 0.84(2) 2.14(3) 2.955(4) 164(3) 4_556 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 C1 C2 C3 C4 -1.3(6) . . . . ? C1 C6 C7 C8 94.0(3) . . . . ? C1 C6 C7 N2 -32.1(4) . . . . ? C2 C1 C6 C5 -1.4(5) . . . . ? C2 C1 C6 C7 178.8(3) . . . . ? C2 C3 C4 C5 0.0(7) . . . . ? C3 C4 C5 C6 0.6(7) . . . . ? C4 C5 C6 C1 0.2(6) . . . . ? C4 C5 C6 C7 -180.0(4) . . . . ? C5 C6 C7 C8 -85.8(3) . . . . ? C5 C6 C7 N2 148.1(3) . . . . ? C6 C1 C2 C3 2.0(6) . . . . ? C6 C1 C2 Cl1 -179.2(2) . . . . ? C6 C7 C8 C9 -26.0(3) . . . . ? C6 C7 C8 C10 87.8(3) . . . . ? C6 C7 C8 C16 -144.1(2) . . . . ? C6 C7 N2 C17 165.2(2) . . . . ? C7 C8 C9 N1 118.0(2) . . . . ? C7 C8 C9 O1 -63.1(3) . . . . ? C7 C8 C10 C11 -119.0(2) . . . . ? C7 C8 C10 C15 57.9(4) . . . . ? C7 C8 C16 C17 -11.2(2) . . . . ? C7 C8 C16 C18 -139.9(3) . . . . ? C8 C7 N2 C17 34.5(3) . . . . ? C8 C9 N1 C11 -0.1(3) . . . . ? C8 C10 C11 C12 179.0(3) . . . . ? C8 C10 C11 N1 -1.4(3) . . . . ? C8 C10 C15 C14 -178.9(3) . . . . ? C8 C16 C17 C21 150.8(3) . . . . ? C8 C16 C17 N2 32.8(3) . . . . ? C8 C16 C18 C19 -62.1(4) . . . . ? C8 C16 C18 C20 175.6(3) . . . . ? C9 C8 C10 C11 1.3(3) . . . . ? C9 C8 C10 C15 178.1(3) . . . . ? C9 C8 C16 C17 -131.2(2) . . . . ? C9 C8 C16 C18 100.0(3) . . . . ? C10 C8 C9 N1 -0.7(3) . . . . ? C10 C8 C9 O1 178.1(3) . . . . ? C10 C8 C16 C17 111.3(3) . . . . ? C10 C8 C16 C18 -17.5(4) . . . . ? C10 C11 C12 C13 0.2(5) . . . . ? C10 C11 N1 C9 1.0(3) . . . . ? C11 C10 C15 C14 -2.3(4) . . . . ? C11 C12 C13 C14 -1.5(6) . . . . ? C12 C11 N1 C9 -179.5(3) . . . . ? C12 C13 C14 C15 0.8(6) . . . . ? C13 C14 C15 C10 1.1(5) . . . . ? C15 C10 C11 C12 1.7(4) . . . . ? C15 C10 C11 N1 -178.7(3) . . . . ? C16 C8 C9 N1 -128.2(2) . . . . ? C16 C8 C9 O1 50.6(3) . . . . ? C16 C8 C10 C11 122.6(3) . . . . ? C16 C8 C10 C15 -60.5(4) . . . . ? C16 C17 C21 O2 -52.2(5) . . . . ? C16 C17 C21 O3 131.2(3) . . . . ? C16 C17 N2 C7 -42.4(3) . . . . ? C17 C16 C18 C19 175.6(3) . . . . ? C17 C16 C18 C20 53.3(4) . . . . ? C17 C21 O3 C22 -178.5(6) . . . . ? C18 C16 C17 C21 -81.0(3) . . . . ? C18 C16 C17 N2 161.0(2) . . . . ? C21 C17 N2 C7 -164.4(3) . . . . ? Cl1 C2 C3 C4 179.9(4) . . . . ? N1 C11 C12 C13 -179.3(3) . . . . ? N2 C7 C8 C9 104.3(2) . . . . ? N2 C7 C8 C10 -141.9(2) . . . . ? N2 C7 C8 C16 -13.8(3) . . . . ? N2 C17 C21 O2 64.6(5) . . . . ? N2 C17 C21 O3 -112.0(4) . . . . ? O1 C9 N1 C11 -179.0(3) . . . . ? O2 C21 O3 C22 4.9(8) . . . . ? loop_ _smtbx_masks_void_nr _smtbx_masks_void_average_x _smtbx_masks_void_average_y _smtbx_masks_void_average_z _smtbx_masks_void_volume _smtbx_masks_void_count_electrons _smtbx_masks_void_content 1 0.000 0.154 -0.402 316.3 62.3 ? 2 0.500 0.654 0.694 316.3 62.3 ?