#------------------------------------------------------------------------------ #$Date: 2020-06-03 05:53:35 +0300 (Wed, 03 Jun 2020) $ #$Revision: 252561 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/05/7240594.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_7240594 loop_ _publ_author_name 'Poirier, Marion' 'Pujol-Gim\'enez, Jonai' 'Manatschal, Cristina' 'B\"uhlmann, Sven' 'Embaby, Ahmed' 'Javor, Sacha' 'Hediger, Matthias A.' 'Reymond, Jean-Louis' _publ_section_title ; Pyrazolyl-pyrimidones inhibit the function of human solute carrier protein SLC11A2 (hDMT1) by metal chelation ; _journal_name_full 'RSC Medicinal Chemistry' _journal_paper_doi 10.1039/D0MD00085J _journal_year 2020 _chemical_absolute_configuration unk _chemical_formula_moiety 'Cl, C10 H13 N4 O2, H2 O' _chemical_formula_sum 'C10 H15 Cl N4 O3' _chemical_formula_weight 274.71 _chemical_name_systematic 6-ethyl-4-hydroxy-2-(3-methyl-5-oxo-2,5-dihydro-1H-pyrazol-1-yl)pyrimidin-1-ium _space_group_crystal_system monoclinic _space_group_IT_number 4 _space_group_name_Hall 'P 2yb' _space_group_name_H-M_alt 'P 1 21 1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary dual _audit_creation_date 2020-01-07 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2020-01-10 deposited with the CCDC. 2020-05-07 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90.8062(4) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 8.66205(5) _cell_length_b 14.39226(6) _cell_length_c 9.94738(4) _cell_measurement_reflns_used 36763 _cell_measurement_temperature 173.01(10) _cell_measurement_theta_max 77.0270 _cell_measurement_theta_min 4.4440 _cell_volume 1239.982(10) _computing_cell_refinement 'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)' _computing_data_collection 'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)' _computing_data_reduction 'CrysAlisPro 1.171.40.45a (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 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 173.01(10) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 10.0000 _diffrn_detector_type HyPix _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.992 _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 -31.00 54.00 0.50 0.20 -- -18.75 45.00 -30.00 170 2 \w 8.00 35.00 0.50 0.20 -- 38.00 93.00 57.22 54 3 \w 4.00 35.00 0.50 0.20 -- 34.00 93.00 117.01 62 4 \w 27.00 122.00 0.50 0.20 -- 50.00 78.00 140.63 190 5 \w 81.00 167.00 0.50 0.40 -- 94.00 49.00 97.72 172 6 \w 104.00 171.00 0.50 0.40 -- 107.11 109.00 124.00 134 7 \w 91.00 171.00 0.50 0.40 -- 107.11 61.00 120.00 160 8 \w 91.00 171.00 0.50 0.40 -- 107.11 61.00 -30.00 160 9 \w 91.00 171.00 0.50 0.40 -- 107.11 61.00 30.00 160 10 \w 95.00 171.00 0.50 0.40 -- 107.11 45.00 0.00 152 11 \w 91.00 171.00 0.50 0.40 -- 107.11 61.00 150.00 160 12 \w 95.00 171.00 0.50 0.40 -- 107.11 125.00 30.00 152 13 \w 91.00 171.00 0.50 0.40 -- 107.11 61.00 -60.00 160 14 \w 90.00 171.00 0.50 0.40 -- 107.11 63.00-140.79 162 15 \w 91.00 171.00 0.50 0.40 -- 107.11 61.00 -90.00 160 16 \w 85.00 171.00 0.50 0.40 -- 107.11 77.00 90.00 172 17 \w 85.00 171.00 0.50 0.40 -- 107.11 77.00 -60.00 172 18 \w 85.00 171.00 0.50 0.40 -- 107.11 77.00-180.00 172 19 \w 85.00 171.00 0.50 0.40 -- 107.11 77.00 0.00 172 20 \w 85.00 171.00 0.50 0.40 -- 107.11 77.00 30.00 172 21 \w 85.00 171.00 0.50 0.40 -- 107.11 77.00 120.00 172 22 \w 64.00 154.00 0.50 0.40 -- 82.00 66.00 113.84 180 23 \w 71.00 159.00 0.50 0.40 -- 86.00 57.00 85.17 176 24 \w 68.00 159.00 0.50 0.40 -- 86.00 67.00-106.51 182 25 \w 66.00 159.00 0.50 0.40 -- 86.00 72.00-166.24 186 26 \w 71.00 159.00 0.50 0.40 -- 86.00 57.00-125.37 176 27 \w 64.00 159.00 0.50 0.40 -- 86.00 76.00 2.34 190 28 \w 74.00 162.00 0.50 0.40 -- 90.00 61.00 -58.80 176 29 \w 57.00 146.00 0.50 0.20 -- 74.00 64.00-176.65 178 30 \w 59.00 151.00 0.50 0.40 -- 78.00 69.00 -52.42 184 31 \w 62.00 154.00 0.50 0.40 -- 82.00 72.00 -88.07 184 32 \w 60.00 154.00 0.50 0.40 -- 82.00 76.00 -70.45 188 33 \w 61.00 154.00 0.50 0.40 -- 82.00 73.00 52.23 186 34 \w 48.00 143.00 0.50 0.20 -- 70.00 75.00 100.33 190 35 \w 51.00 143.00 0.50 0.20 -- 70.00 68.00 74.46 184 36 \w 48.00 143.00 0.50 0.20 -- 70.00 75.00 175.91 190 37 \w 36.00 131.00 0.50 0.20 -- 58.00 77.00 74.11 190 38 \w 53.00 146.00 0.50 0.20 -- 74.00 74.00 -61.20 186 39 \w 40.00 135.00 0.50 0.20 -- 62.00 77.00 147.26 190 40 \w 40.00 135.00 0.50 0.20 -- 62.00 75.00 27.42 190 41 \w 40.00 135.00 0.50 0.20 -- 62.00 75.00 -62.85 190 42 \w 44.00 139.00 0.50 0.20 -- 66.00 76.00 46.67 190 43 \w 44.00 139.00 0.50 0.20 -- 66.00 76.00 123.93 190 44 \w 44.00 139.00 0.50 0.20 -- 66.00 75.00 172.98 190 45 \w 44.00 139.00 0.50 0.20 -- 66.00 75.00 1.82 190 46 \w 47.00 143.00 0.50 0.20 -- 70.00 78.00-105.75 192 47 \w 39.00 135.00 0.50 0.20 -- 62.00 79.00-140.31 192 48 \w 43.00 139.00 0.50 0.20 -- 66.00 78.00-108.91 192 49 \w 34.00 131.00 0.50 0.20 -- 58.00 80.00 -32.51 194 50 \w 42.00 139.00 0.50 0.20 -- 66.00 80.00 -25.55 194 51 \w 35.00 68.00 0.50 0.40 -- 107.11 -61.00 0.00 66 52 \w 35.00 108.00 0.50 0.40 -- 107.11-109.00 28.00 146 53 \w 35.00 96.00 0.50 0.20 -- 47.70-125.00 -60.00 122 54 \w 35.00 112.00 0.50 0.40 -- 107.11-125.00 -30.00 154 55 \w 35.00 112.00 0.50 0.40 -- 107.11-125.00-120.00 154 56 \w 35.00 112.00 0.50 0.40 -- 107.11-125.00 -90.00 154 57 \w 35.00 106.00 0.50 0.40 -- 107.11 -94.00 -30.00 142 58 \w 23.00 87.00 0.50 0.20 -- 47.70-109.00 28.00 128 59 \w 35.00 106.00 0.50 0.40 -- 107.11 -94.00 120.00 142 60 \w 35.00 106.00 0.50 0.40 -- 107.11 -94.00 90.00 142 61 \w 35.00 102.00 0.50 0.40 -- 107.11 -77.00 120.00 134 62 \w 35.00 68.00 0.50 0.40 -- 107.11 -61.00 30.00 66 63 \w 35.00 68.00 0.50 0.40 -- 107.11 -61.00 60.00 66 64 \w 35.00 68.00 0.50 0.40 -- 107.11 -61.00 150.00 66 65 \w -1.00 82.00 0.50 0.20 -- 47.70 -99.00 0.00 166 66 \w 17.00 43.00 0.50 0.20 -- 42.00 83.00 15.12 52 67 \w 10.00 43.00 0.50 0.20 -- 38.00 90.00 -66.64 66 68 \w 28.00 122.00 0.50 0.20 -- 50.00 77.00-139.68 188 69 \w 31.00 126.00 0.50 0.20 -- 54.00 79.00-130.72 190 70 \w 30.00 126.00 0.50 0.20 -- 54.00 80.00 111.97 192 71 \w 27.00 122.00 0.50 0.20 -- 50.00 79.00 179.41 190 72 \w -5.00 29.00 0.50 0.20 -- 26.00 96.00 -33.82 68 73 \w -57.00 0.00 0.50 0.20 -- -18.75 109.00 124.00 114 74 \w -90.00 -3.00 0.50 0.20 -- -18.75 -57.00-150.00 174 75 \w -90.00 -2.00 0.50 0.20 -- -18.75 -61.00 30.00 176 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB Synergy, Dualflex, HyPix' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0330798000 _diffrn_orient_matrix_UB_12 -0.0242020000 _diffrn_orient_matrix_UB_13 -0.1476781000 _diffrn_orient_matrix_UB_21 -0.0472268000 _diffrn_orient_matrix_UB_22 -0.1015539000 _diffrn_orient_matrix_UB_23 0.0261567000 _diffrn_orient_matrix_UB_31 -0.1682360000 _diffrn_orient_matrix_UB_32 0.0237219000 _diffrn_orient_matrix_UB_33 -0.0386779000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0300 _diffrn_reflns_av_unetI/netI 0.0133 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.992 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 53002 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.972 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 76.972 _diffrn_reflns_theta_min 4.445 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'PhotonJet (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 2.824 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.54013 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.40.45a (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.472 _exptl_crystal_description irregular _exptl_crystal_F_000 576 _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.153 _refine_diff_density_min -0.192 _refine_diff_density_rms 0.045 _refine_ls_abs_structure_details ; Flack x determined using 2249 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.004(3) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 350 _refine_ls_number_reflns 5090 _refine_ls_number_restraints 7 _refine_ls_restrained_S_all 1.071 _refine_ls_R_factor_all 0.0258 _refine_ls_R_factor_gt 0.0242 _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^)+(0.0305P)^2^+0.2736P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0589 _refine_ls_wR_factor_ref 0.0604 _reflns_Friedel_coverage 0.883 _reflns_Friedel_fraction_full 0.995 _reflns_Friedel_fraction_max 0.951 _reflns_number_gt 4976 _reflns_number_total 5090 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0md00085j3.cif _cod_data_source_block 19JLR010_MP303A1 _cod_original_cell_volume 1239.982(9) _cod_database_code 7240594 _shelx_shelxl_version_number 2014/7 _chemical_oxdiff_formula 'C40 H40 N8 O8 Cl8 ' _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 0.872 _shelx_estimated_absorpt_t_min 0.602 _reflns_odcompleteness_completeness 100.00 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All N(H) groups At 1.5 times of: All C(H,H,H) groups, All O(H) groups 2. Restrained distances O14-H14 0.82 with sigma of 0.001 H33B-H33A 1.44 with sigma of 0.02 H34B-H34A 1.44 with sigma of 0.02 O33-H33B 0.95 with sigma of 0.02 H34B-O34 0.95 with sigma of 0.02 H33B-H14 \\sim H14-H33A with sigma of 0.02 3.a Secondary CH2 refined with riding coordinates: C15(H15A,H15B), C31(H31A,H31B) 3.b Aromatic/amide H refined with riding coordinates: N27(H27), N11(H11), N4(H4), N19(H19), C25(H25), C9(H9), C2(H2), C17(H17) 3.c Idealised Me refined as rotating group: C32(H32A,H32B,H32C), C16(H16A,H16B,H16C), C13(H13A,H13B,H13C), C29(H29A,H29B, H29C) 3.d Idealised tetrahedral OH refined as rotating group: O30(H30) ; _shelx_res_file ; 19jlr010_c2.res created by SHELXL-2014/7 TITL 19jlr010_c2_a.res in P2(1) REM Old TITL 19JLR010_C2 in P2(1)/m REM SHELXT solution in P2(1) REM R1 0.120, Rweak 0.019, Alpha 0.000, Orientation as input REM Flack x = 0.068 ( 0.016 ) from Parsons' quotients REM Formula found by SHELXT: C25 N5 O4 Cl2 CELL 1.54184 8.662046 14.392259 9.947382 90 90.8062 90 ZERR 4 0.000045 0.000058 0.000037 0 0.0004 0 LATT -1 SYMM -X,0.5+Y,-Z SFAC C H Cl N O UNIT 40 60 4 16 12 DFIX 0.82 0.001 O14 H14 DFIX 1.44 H33b H33a DFIX 1.44 H34b H34a DFIX 0.95 O33 H33b DFIX 0.95 H34b O34 SADI H33b H14 H14 H33a L.S. 40 PLAN 5 SIZE 0.2 0.1 0.05 BOND $H list 4 fmap 2 53 acta OMIT -1 6 2 OMIT 9 5 5 OMIT 7 -9 6 REM REM REM WGHT 0.030500 0.273600 FVAR 0.29700 CL2 3 0.522565 0.274521 0.941808 11.00000 0.03576 0.02234 = 0.03396 0.00136 0.00683 -0.00132 CL1 3 0.085629 0.517230 0.986148 11.00000 0.03397 0.02262 = 0.03626 0.00223 0.01011 -0.00147 O14 5 0.404818 0.429742 0.614487 11.00000 0.04159 0.01736 = 0.02909 0.00126 0.01257 -0.00011 O12 5 0.353007 0.866855 0.643274 11.00000 0.03648 0.01799 = 0.04154 0.00221 0.01249 -0.00243 O28 5 0.875967 0.622389 0.655748 11.00000 0.04019 0.01842 = 0.03600 0.00143 0.01120 -0.00379 O30 5 0.885707 0.185668 0.599060 11.00000 0.03876 0.01753 = 0.03186 0.00143 0.01421 0.00031 AFIX 147 H30 2 0.832142 0.175034 0.664611 11.00000 -1.50000 AFIX 0 O34 5 0.731072 0.132714 0.794540 11.00000 0.03933 0.02509 = 0.03367 0.00468 0.01156 0.00138 O33 5 0.246767 0.374266 0.804004 11.00000 0.03917 0.02493 = 0.03294 0.00213 0.01257 0.00068 N23 4 0.835335 0.331243 0.675090 11.00000 0.02616 0.01926 = 0.02448 0.00027 0.00400 0.00151 N7 4 0.333387 0.575201 0.677740 11.00000 0.02627 0.01907 = 0.02456 0.00023 0.00369 0.00087 N27 4 0.953755 0.457971 0.565998 11.00000 0.02710 0.01700 = 0.02588 0.00034 0.00517 -0.00048 AFIX 43 H27 2 0.966027 0.517207 0.562279 11.00000 -1.20000 AFIX 0 N11 4 0.446888 0.702481 0.566374 11.00000 0.02717 0.01694 = 0.02818 0.00056 0.00574 -0.00119 AFIX 43 H11 2 0.454101 0.761894 0.559697 11.00000 -1.20000 AFIX 0 N5 4 0.272884 0.726394 0.734578 11.00000 0.02692 0.01705 = 0.02753 -0.00079 0.00901 -0.00094 N4 4 0.173304 0.698111 0.832835 11.00000 0.03074 0.01841 = 0.02744 0.00082 0.01031 -0.00037 AFIX 43 H4 2 0.152920 0.641591 0.854318 11.00000 -1.20000 AFIX 0 N20 4 0.787580 0.482208 0.740515 11.00000 0.03019 0.01706 = 0.02425 -0.00093 0.00912 -0.00059 N19 4 0.693127 0.453649 0.842825 11.00000 0.03142 0.01926 = 0.02765 -0.00086 0.01079 -0.00153 AFIX 43 H19 2 0.673844 0.397100 0.864920 11.00000 -1.20000 AFIX 0 C8 1 0.417853 0.518844 0.598956 11.00000 0.02877 0.01839 = 0.02389 -0.00084 0.00186 0.00040 C24 1 0.908854 0.274890 0.589150 11.00000 0.02731 0.01828 = 0.02452 0.00014 0.00331 0.00258 C10 1 0.531550 0.646149 0.483693 11.00000 0.02209 0.02240 = 0.02231 0.00070 0.00065 0.00000 C25 1 1.008253 0.308379 0.488248 11.00000 0.02557 0.02112 = 0.02487 -0.00143 0.00519 0.00262 AFIX 43 H25 2 1.058077 0.267512 0.430871 11.00000 -1.20000 AFIX 0 C9 1 0.517943 0.552815 0.499164 11.00000 0.02824 0.02183 = 0.02403 -0.00172 0.00519 0.00083 AFIX 43 H9 2 0.573165 0.512142 0.445381 11.00000 -1.20000 AFIX 0 C26 1 1.029050 0.401313 0.477271 11.00000 0.02297 0.02409 = 0.02116 0.00097 0.00090 0.00069 C22 1 0.860521 0.420555 0.658987 11.00000 0.02438 0.02021 = 0.02179 -0.00033 0.00234 0.00107 C1 1 0.273672 0.825418 0.728402 11.00000 0.02807 0.01768 = 0.03103 0.00057 0.00034 0.00088 C21 1 0.794617 0.580983 0.738478 11.00000 0.03118 0.01557 = 0.02951 -0.00149 0.00052 0.00026 C6 1 0.352561 0.664550 0.657921 11.00000 0.02220 0.02046 = 0.02388 -0.00122 0.00247 0.00074 C32 1 1.236483 0.386963 0.300057 11.00000 0.03196 0.03142 = 0.03238 0.00375 0.01182 0.00286 AFIX 137 H32A 2 1.289481 0.422343 0.233149 11.00000 -1.50000 H32B 2 1.180933 0.337011 0.257530 11.00000 -1.50000 H32C 2 1.310155 0.362007 0.363371 11.00000 -1.50000 AFIX 0 C15 1 0.629542 0.694781 0.383538 11.00000 0.02973 0.02522 = 0.02750 0.00359 0.00495 -0.00178 AFIX 23 H15A 2 0.688254 0.742852 0.429623 11.00000 -1.20000 H15B 2 0.562505 0.725088 0.318071 11.00000 -1.20000 AFIX 0 C16 1 0.740902 0.632546 0.309437 11.00000 0.03584 0.03492 = 0.03179 0.00216 0.01254 0.00043 AFIX 137 H16A 2 0.795176 0.668449 0.243904 11.00000 -1.50000 H16B 2 0.684525 0.583672 0.265114 11.00000 -1.50000 H16C 2 0.813558 0.606089 0.372347 11.00000 -1.50000 AFIX 0 C31 1 1.123736 0.449626 0.373169 11.00000 0.02623 0.02205 = 0.02713 0.00221 0.00431 -0.00085 AFIX 23 H31A 2 1.181399 0.499379 0.416374 11.00000 -1.20000 H31B 2 1.054414 0.477662 0.307355 11.00000 -1.20000 AFIX 0 C2 1 0.170787 0.852923 0.828660 11.00000 0.02902 0.01845 = 0.03013 -0.00149 0.00177 0.00445 AFIX 43 H2 2 0.145591 0.913858 0.850413 11.00000 -1.20000 AFIX 0 C17 1 0.694921 0.608703 0.842646 11.00000 0.02762 0.01971 = 0.03279 -0.00519 0.00321 0.00172 AFIX 43 H17 2 0.672708 0.669614 0.866870 11.00000 -1.20000 AFIX 0 C3 1 0.113598 0.774563 0.889224 11.00000 0.02564 0.02333 = 0.02509 -0.00257 0.00163 0.00390 C18 1 0.636602 0.530152 0.901826 11.00000 0.02451 0.02253 = 0.02678 -0.00494 0.00295 0.00136 C13 1 0.002108 0.765693 1.001111 11.00000 0.03793 0.02652 = 0.02955 -0.00003 0.01105 0.00554 AFIX 137 H13A 2 -0.025934 0.701618 1.011861 11.00000 -1.50000 H13B 2 -0.088612 0.801622 0.980710 11.00000 -1.50000 H13C 2 0.049002 0.788123 1.082886 11.00000 -1.50000 AFIX 0 C29 1 0.524671 0.521363 1.012838 11.00000 0.03194 0.02681 = 0.03518 -0.00574 0.01240 -0.00186 AFIX 137 H29A 2 0.422020 0.516172 0.975958 11.00000 -1.50000 H29B 2 0.531179 0.575308 1.069398 11.00000 -1.50000 H29C 2 0.548461 0.466929 1.064917 11.00000 -1.50000 AFIX 0 H33A 2 0.316078 0.341096 0.863846 11.00000 0.07868 H14 2 0.345434 0.412173 0.672743 11.00000 0.06975 H33B 2 0.206670 0.415301 0.858254 11.00000 0.04772 H34A 2 0.778016 0.100074 0.852982 11.00000 0.05865 H34B 2 0.664410 0.171004 0.832181 11.00000 0.06315 HKLF 4 REM 19jlr010_c2_a.res in P2(1) REM R1 = 0.0242 for 4976 Fo > 4sig(Fo) and 0.0258 for all 5090 data REM 350 parameters refined using 7 restraints END WGHT 0.0305 0.2737 REM Highest difference peak 0.153, deepest hole -0.192, 1-sigma level 0.045 Q1 1 0.5023 0.2799 0.8003 11.00000 0.05 0.15 Q2 1 0.1129 0.7365 1.1032 11.00000 0.05 0.15 Q3 1 0.6315 0.2781 1.0104 11.00000 0.05 0.14 Q4 1 0.1311 0.3626 0.6548 11.00000 0.05 0.13 Q5 1 0.1854 0.5168 1.0334 11.00000 0.05 0.13 ; _shelx_res_checksum 8732 _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 1.640 _oxdiff_exptl_absorpt_empirical_full_min 0.815 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, 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 Cl2 Cl 0.52257(6) 0.27452(3) 0.94181(5) 0.03063(12) Uani 1 1 d . . . . . Cl1 Cl 0.08563(6) 0.51723(3) 0.98615(5) 0.03086(12) Uani 1 1 d . . . . . O14 O 0.4048(2) 0.42974(10) 0.61449(16) 0.0292(3) Uani 1 1 d D . . . . O12 O 0.3530(2) 0.86685(10) 0.64327(18) 0.0319(4) Uani 1 1 d . . . . . O28 O 0.8760(2) 0.62239(10) 0.65575(16) 0.0314(4) Uani 1 1 d . . . . . O30 O 0.88571(19) 0.18567(10) 0.59906(16) 0.0293(3) Uani 1 1 d . . . . . H30 H 0.8321 0.1750 0.6646 0.044 Uiso 1 1 calc GR . . . . O34 O 0.7311(2) 0.13271(11) 0.79454(16) 0.0326(4) Uani 1 1 d D . . . . O33 O 0.2468(2) 0.37427(11) 0.80400(16) 0.0322(4) Uani 1 1 d D . . . . N23 N 0.8353(2) 0.33124(12) 0.67509(17) 0.0233(4) Uani 1 1 d . . . . . N7 N 0.3334(2) 0.57520(12) 0.67774(17) 0.0233(4) Uani 1 1 d . . . . . N27 N 0.9538(2) 0.45797(12) 0.56600(17) 0.0233(4) Uani 1 1 d . . . . . H27 H 0.9660 0.5172 0.5623 0.028 Uiso 1 1 calc R . . . . N11 N 0.4469(2) 0.70248(12) 0.56637(17) 0.0240(4) Uani 1 1 d . . . . . H11 H 0.4541 0.7619 0.5597 0.029 Uiso 1 1 calc R . . . . N5 N 0.2729(2) 0.72639(12) 0.73458(18) 0.0238(4) Uani 1 1 d . . . . . N4 N 0.1733(2) 0.69811(13) 0.83284(18) 0.0254(4) Uani 1 1 d . . . . . H4 H 0.1529 0.6416 0.8543 0.031 Uiso 1 1 calc R . . . . N20 N 0.7876(2) 0.48221(12) 0.74051(17) 0.0238(4) Uani 1 1 d . . . . . N19 N 0.6931(2) 0.45365(12) 0.84283(18) 0.0260(4) Uani 1 1 d . . . . . H19 H 0.6738 0.3971 0.8649 0.031 Uiso 1 1 calc R . . . . C8 C 0.4179(2) 0.51884(15) 0.59896(19) 0.0237(4) Uani 1 1 d . . . . . C24 C 0.9089(2) 0.27489(15) 0.58915(19) 0.0233(4) Uani 1 1 d . . . . . C10 C 0.5315(2) 0.64615(14) 0.48369(19) 0.0223(4) Uani 1 1 d . . . . . C25 C 1.0083(2) 0.30838(14) 0.4882(2) 0.0238(4) Uani 1 1 d . . . . . H25 H 1.0581 0.2675 0.4309 0.029 Uiso 1 1 calc R . . . . C9 C 0.5179(3) 0.55282(14) 0.4992(2) 0.0247(4) Uani 1 1 d . . . . . H9 H 0.5732 0.5121 0.4454 0.030 Uiso 1 1 calc R . . . . C26 C 1.0291(2) 0.40131(14) 0.4773(2) 0.0227(4) Uani 1 1 d . . . . . C22 C 0.8605(2) 0.42055(14) 0.6590(2) 0.0221(4) Uani 1 1 d . . . . . C1 C 0.2737(3) 0.82542(15) 0.7284(2) 0.0256(4) Uani 1 1 d . . . . . C21 C 0.7946(3) 0.58098(14) 0.7385(2) 0.0254(4) Uani 1 1 d . . . . . C6 C 0.3526(2) 0.66455(14) 0.6579(2) 0.0222(4) Uani 1 1 d . . . . . C32 C 1.2365(3) 0.38696(16) 0.3001(2) 0.0318(5) Uani 1 1 d . . . . . H32A H 1.2895 0.4223 0.2331 0.048 Uiso 1 1 calc GR . . . . H32B H 1.1809 0.3370 0.2575 0.048 Uiso 1 1 calc GR . . . . H32C H 1.3102 0.3620 0.3634 0.048 Uiso 1 1 calc GR . . . . C15 C 0.6295(3) 0.69478(16) 0.3835(2) 0.0274(5) Uani 1 1 d . . . . . H15A H 0.6883 0.7429 0.4296 0.033 Uiso 1 1 calc R . . . . H15B H 0.5625 0.7251 0.3181 0.033 Uiso 1 1 calc R . . . . C16 C 0.7409(3) 0.63255(17) 0.3094(2) 0.0341(5) Uani 1 1 d . . . . . H16A H 0.7952 0.6684 0.2439 0.051 Uiso 1 1 calc GR . . . . H16B H 0.6845 0.5837 0.2651 0.051 Uiso 1 1 calc GR . . . . H16C H 0.8136 0.6061 0.3723 0.051 Uiso 1 1 calc GR . . . . C31 C 1.1237(3) 0.44963(14) 0.3732(2) 0.0251(4) Uani 1 1 d . . . . . H31A H 1.1814 0.4994 0.4164 0.030 Uiso 1 1 calc R . . . . H31B H 1.0544 0.4777 0.3074 0.030 Uiso 1 1 calc R . . . . C2 C 0.1708(3) 0.85292(14) 0.8287(2) 0.0259(4) Uani 1 1 d . . . . . H2 H 0.1456 0.9139 0.8504 0.031 Uiso 1 1 calc R . . . . C17 C 0.6949(3) 0.60870(15) 0.8426(2) 0.0267(4) Uani 1 1 d . . . . . H17 H 0.6727 0.6696 0.8669 0.032 Uiso 1 1 calc R . . . . C3 C 0.1136(2) 0.77456(16) 0.88922(19) 0.0247(4) Uani 1 1 d . . . . . C18 C 0.6366(2) 0.53015(15) 0.90183(19) 0.0246(4) Uani 1 1 d . . . . . C13 C 0.0021(3) 0.76569(18) 1.0011(2) 0.0312(4) Uani 1 1 d . . . . . H13A H -0.0259 0.7016 1.0119 0.047 Uiso 1 1 calc GR . . . . H13B H -0.0886 0.8016 0.9807 0.047 Uiso 1 1 calc GR . . . . H13C H 0.0490 0.7881 1.0829 0.047 Uiso 1 1 calc GR . . . . C29 C 0.5247(3) 0.52136(18) 1.0128(2) 0.0312(5) Uani 1 1 d . . . . . H29A H 0.4220 0.5162 0.9760 0.047 Uiso 1 1 calc GR . . . . H29B H 0.5312 0.5753 1.0694 0.047 Uiso 1 1 calc GR . . . . H29C H 0.5485 0.4669 1.0649 0.047 Uiso 1 1 calc GR . . . . H33A H 0.316(4) 0.341(2) 0.864(3) 0.079(12) Uiso 1 1 d D . . . . H14 H 0.345(3) 0.412(2) 0.673(3) 0.070(12) Uiso 1 1 d D . . . . H33B H 0.207(3) 0.4153(18) 0.858(3) 0.048(9) Uiso 1 1 d D . . . . H34A H 0.778(4) 0.100(2) 0.853(3) 0.059(10) Uiso 1 1 d D . . . . H34B H 0.664(3) 0.171(2) 0.832(3) 0.063(11) Uiso 1 1 d 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 Cl2 0.0358(3) 0.0223(2) 0.0340(2) 0.0014(2) 0.00683(19) -0.0013(2) Cl1 0.0340(3) 0.0226(2) 0.0363(2) 0.0022(2) 0.0101(2) -0.0015(2) O14 0.0416(9) 0.0174(7) 0.0291(8) 0.0013(6) 0.0126(7) -0.0001(6) O12 0.0365(9) 0.0180(8) 0.0415(9) 0.0022(6) 0.0125(7) -0.0024(6) O28 0.0402(9) 0.0184(7) 0.0360(9) 0.0014(6) 0.0112(7) -0.0038(7) O30 0.0388(9) 0.0175(7) 0.0319(8) 0.0014(6) 0.0142(7) 0.0003(6) O34 0.0393(10) 0.0251(8) 0.0337(8) 0.0047(7) 0.0116(7) 0.0014(7) O33 0.0392(9) 0.0249(8) 0.0329(8) 0.0021(7) 0.0126(7) 0.0007(7) N23 0.0262(9) 0.0193(8) 0.0245(8) 0.0003(6) 0.0040(7) 0.0015(7) N7 0.0263(9) 0.0191(8) 0.0246(8) 0.0002(7) 0.0037(7) 0.0009(7) N27 0.0271(9) 0.0170(8) 0.0259(8) 0.0003(6) 0.0052(7) -0.0005(7) N11 0.0272(9) 0.0169(8) 0.0282(9) 0.0006(7) 0.0057(7) -0.0012(7) N5 0.0269(10) 0.0171(8) 0.0275(9) -0.0008(6) 0.0090(7) -0.0009(7) N4 0.0307(10) 0.0184(8) 0.0274(9) 0.0008(7) 0.0103(7) -0.0004(7) N20 0.0302(10) 0.0171(8) 0.0242(8) -0.0009(6) 0.0091(7) -0.0006(7) N19 0.0314(10) 0.0193(8) 0.0276(9) -0.0009(7) 0.0108(8) -0.0015(7) C8 0.0288(10) 0.0184(9) 0.0239(9) -0.0008(8) 0.0019(7) 0.0004(9) C24 0.0273(10) 0.0183(9) 0.0245(9) 0.0001(8) 0.0033(7) 0.0026(9) C10 0.0221(10) 0.0224(10) 0.0223(9) 0.0007(8) 0.0006(7) 0.0000(8) C25 0.0256(10) 0.0211(9) 0.0249(9) -0.0014(8) 0.0052(8) 0.0026(8) C9 0.0282(11) 0.0218(10) 0.0240(9) -0.0017(8) 0.0052(8) 0.0008(8) C26 0.0230(10) 0.0241(10) 0.0212(9) 0.0010(7) 0.0009(8) 0.0007(8) C22 0.0244(10) 0.0202(10) 0.0218(10) -0.0003(8) 0.0023(8) 0.0011(8) C1 0.0281(11) 0.0177(10) 0.0310(11) 0.0006(8) 0.0003(9) 0.0009(8) C21 0.0312(12) 0.0156(9) 0.0295(10) -0.0015(8) 0.0005(9) 0.0003(8) C6 0.0222(10) 0.0205(10) 0.0239(10) -0.0012(7) 0.0025(8) 0.0007(8) C32 0.0320(12) 0.0314(12) 0.0324(11) 0.0037(9) 0.0118(9) 0.0029(9) C15 0.0297(11) 0.0252(11) 0.0275(11) 0.0036(9) 0.0050(9) -0.0018(9) C16 0.0358(13) 0.0349(12) 0.0318(11) 0.0022(10) 0.0125(9) 0.0004(10) C31 0.0262(11) 0.0220(10) 0.0271(10) 0.0022(8) 0.0043(8) -0.0008(8) C2 0.0290(11) 0.0185(10) 0.0301(10) -0.0015(8) 0.0018(9) 0.0045(8) C17 0.0276(11) 0.0197(10) 0.0328(11) -0.0052(8) 0.0032(9) 0.0017(8) C3 0.0256(10) 0.0233(9) 0.0251(9) -0.0026(9) 0.0016(7) 0.0039(9) C18 0.0245(10) 0.0225(10) 0.0268(9) -0.0049(8) 0.0029(8) 0.0014(8) C13 0.0379(11) 0.0265(10) 0.0295(9) 0.0000(9) 0.0110(8) 0.0055(9) C29 0.0319(12) 0.0268(10) 0.0352(10) -0.0057(10) 0.0124(9) -0.0019(10) 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 C8 O14 H14 116(2) . . ? C24 O30 H30 109.5 . . ? H34A O34 H34B 111(3) . . ? H33A O33 H33B 102(2) . . ? C22 N23 C24 115.56(18) . . ? C6 N7 C8 115.52(17) . . ? C26 N27 H27 120.1 . . ? C22 N27 H27 120.1 . . ? C22 N27 C26 119.88(17) . . ? C10 N11 H11 120.0 . . ? C6 N11 H11 120.0 . . ? C6 N11 C10 119.95(17) . . ? N4 N5 C1 109.27(17) . . ? C6 N5 N4 122.09(17) . . ? C6 N5 C1 128.64(19) . . ? N5 N4 H4 126.2 . . ? C3 N4 N5 107.69(17) . . ? C3 N4 H4 126.2 . . ? N19 N20 C21 109.55(17) . . ? C22 N20 N19 122.03(17) . . ? C22 N20 C21 128.42(19) . . ? N20 N19 H19 126.2 . . ? C18 N19 N20 107.59(17) . . ? C18 N19 H19 126.2 . . ? O14 C8 N7 118.43(17) . . ? O14 C8 C9 118.73(18) . . ? N7 C8 C9 122.83(19) . . ? O30 C24 N23 118.11(18) . . ? O30 C24 C25 118.98(18) . . ? N23 C24 C25 122.90(19) . . ? N11 C10 C15 115.86(18) . . ? C9 C10 N11 117.91(18) . . ? C9 C10 C15 126.2(2) . . ? C24 C25 H25 120.8 . . ? C26 C25 C24 118.44(19) . . ? C26 C25 H25 120.8 . . ? C8 C9 H9 120.8 . . ? C10 C9 C8 118.47(19) . . ? C10 C9 H9 120.8 . . ? N27 C26 C31 115.94(17) . . ? C25 C26 N27 118.02(18) . . ? C25 C26 C31 126.00(19) . . ? N23 C22 N27 125.19(19) . . ? N23 C22 N20 119.02(18) . . ? N27 C22 N20 115.79(18) . . ? O12 C1 N5 120.6(2) . . ? O12 C1 C2 135.0(2) . . ? C2 C1 N5 104.34(19) . . ? O28 C21 N20 120.9(2) . . ? O28 C21 C17 135.0(2) . . ? C17 C21 N20 104.15(19) . . ? N7 C6 N11 125.30(19) . . ? N7 C6 N5 119.27(19) . . ? N11 C6 N5 115.42(18) . . ? H32A C32 H32B 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? C10 C15 H15A 108.6 . . ? C10 C15 H15B 108.6 . . ? C10 C15 C16 114.80(18) . . ? H15A C15 H15B 107.5 . . ? C16 C15 H15A 108.6 . . ? C16 C15 H15B 108.6 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16B 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C26 C31 C32 114.57(17) . . ? C26 C31 H31A 108.6 . . ? C26 C31 H31B 108.6 . . ? C32 C31 H31A 108.6 . . ? C32 C31 H31B 108.6 . . ? H31A C31 H31B 107.6 . . ? C1 C2 H2 125.8 . . ? C3 C2 C1 108.44(18) . . ? C3 C2 H2 125.8 . . ? C21 C17 H17 125.9 . . ? C18 C17 C21 108.27(18) . . ? C18 C17 H17 125.9 . . ? N4 C3 C2 110.26(17) . . ? N4 C3 C13 120.0(2) . . ? C2 C3 C13 129.8(2) . . ? N19 C18 C17 110.41(17) . . ? N19 C18 C29 120.1(2) . . ? C17 C18 C29 129.5(2) . . ? C3 C13 H13A 109.5 . . ? C3 C13 H13B 109.5 . . ? C3 C13 H13C 109.5 . . ? H13A C13 H13B 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C18 C29 H29A 109.5 . . ? C18 C29 H29B 109.5 . . ? C18 C29 H29C 109.5 . . ? H29A C29 H29B 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? 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 O14 C8 1.297(3) . ? O14 H14 0.8202(15) . ? O12 C1 1.250(3) . ? O28 C21 1.243(3) . ? O30 H30 0.8200 . ? O30 C24 1.304(3) . ? O34 H34A 0.85(3) . ? O34 H34B 0.89(2) . ? O33 H33A 0.97(3) . ? O33 H33B 0.88(2) . ? N23 C24 1.345(3) . ? N23 C22 1.314(3) . ? N7 C8 1.350(3) . ? N7 C6 1.312(3) . ? N27 H27 0.8600 . ? N27 C26 1.373(3) . ? N27 C22 1.349(3) . ? N11 H11 0.8600 . ? N11 C10 1.374(3) . ? N11 C6 1.348(3) . ? N5 N4 1.374(2) . ? N5 C1 1.427(2) . ? N5 C6 1.366(3) . ? N4 H4 0.8600 . ? N4 C3 1.342(3) . ? N20 N19 1.378(2) . ? N20 C22 1.363(3) . ? N20 C21 1.423(3) . ? N19 H19 0.8600 . ? N19 C18 1.343(3) . ? C8 C9 1.414(3) . ? C24 C25 1.416(3) . ? C10 C9 1.357(3) . ? C10 C15 1.492(3) . ? C25 H25 0.9300 . ? C25 C26 1.354(3) . ? C9 H9 0.9300 . ? C26 C31 1.501(3) . ? C1 C2 1.404(3) . ? C21 C17 1.416(3) . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? C32 C31 1.522(3) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C15 C16 1.515(3) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? C2 H2 0.9300 . ? C2 C3 1.374(3) . ? C17 H17 0.9300 . ? C17 C18 1.374(3) . ? C3 C13 1.489(3) . ? C18 C29 1.485(3) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ?