#------------------------------------------------------------------------------ #$Date: 2024-01-06 10:21:58 +0200 (Sat, 06 Jan 2024) $ #$Revision: 288817 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/76/7247607.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_7247607 loop_ _publ_author_name 'Li, Chaoyang' 'Niu, Xinyue' 'Xu, Wan' 'Bu, Zhanwei' 'Zhang, Wenjing' 'Wang, Qilin' _publ_section_title ; Distinct reactivities of ortho-chalcone-substituted organophosphines with activated alkynes: skeletal editing or periphery modification ; _journal_issue 24 _journal_name_full 'Green Chemistry' _journal_page_first 10587 _journal_page_last 10595 _journal_paper_doi 10.1039/D3GC03165A _journal_volume 25 _journal_year 2023 _chemical_formula_moiety 'C33 H26 Cl O5 P' _chemical_formula_sum 'C33 H26 Cl O5 P' _chemical_formula_weight 568.96 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2022-07-03 _audit_creation_method ; Olex2 1.5-beta (compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439) ; _audit_update_record ; 2022-08-05 deposited with the CCDC. 2023-10-30 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 106.572(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 14.9304(2) _cell_length_b 9.09920(10) _cell_length_c 21.2031(3) _cell_measurement_reflns_used 7992 _cell_measurement_temperature 170(2) _cell_measurement_theta_max 71.3010 _cell_measurement_theta_min 3.0820 _cell_volume 2760.89(7) _computing_cell_refinement 'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)' _computing_data_collection 'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)' _computing_data_reduction 'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)' _computing_molecular_graphics 'Olex2 1.5-beta (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5-beta (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2017/1 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 170(2) _diffrn_detector 'CCD plate' _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.972 _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 -47.00 60.00 0.50 0.50 -- 42.30 -57.00 -30.00 214 2 \w 80.00 105.00 0.50 0.50 -- 42.30 77.00 120.00 50 3 \w 15.00 86.00 0.50 0.50 -- 42.30 -82.00 120.00 142 4 \w -26.00 9.00 0.50 0.50 -- 42.30 -82.00 120.00 70 5 \w 86.00 132.00 0.50 0.50 -- 42.30 77.00 30.00 92 6 \w 96.00 122.00 0.50 0.50 -- 42.30 77.00-180.00 52 7 \w 14.00 55.00 0.50 0.50 -- 101.60 -38.00 -30.00 82 8 \w 92.00 127.00 0.50 0.50 -- 101.60 -82.00-120.00 70 9 \w 58.00 97.00 0.50 0.50 -- 101.60 -82.00 150.00 78 10 \w 30.00 191.00 0.50 0.50 -- 101.60 25.00 150.00 322 11 \w 17.00 132.00 0.50 0.50 -- 101.60 -63.00-150.00 230 12 \w 42.00 142.00 0.50 0.50 -- 101.60 -82.00-150.00 200 13 \w 12.00 146.00 0.50 0.50 -- 101.60 -25.00-180.00 268 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB AFC12 (RINC): Kappa single' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.1062183000 _diffrn_orient_matrix_UB_12 0.0033419000 _diffrn_orient_matrix_UB_13 0.0330293000 _diffrn_orient_matrix_UB_21 0.0174581000 _diffrn_orient_matrix_UB_22 -0.0201478000 _diffrn_orient_matrix_UB_23 -0.0677353000 _diffrn_orient_matrix_UB_31 0.0000831000 _diffrn_orient_matrix_UB_32 0.1679071000 _diffrn_orient_matrix_UB_33 -0.0088286000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0275 _diffrn_reflns_av_unetI/netI 0.0327 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.972 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 13610 _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 71.650 _diffrn_reflns_theta_min 3.088 _diffrn_source 'Rotating-anode X-ray tube' _diffrn_source_type 'Rigaku (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 2.119 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.74182 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear light yellow' _exptl_crystal_density_diffrn 1.369 _exptl_crystal_description block _exptl_crystal_F_000 1184 _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.312 _refine_diff_density_min -0.391 _refine_diff_density_rms 0.046 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 363 _refine_ls_number_reflns 5251 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.053 _refine_ls_R_factor_all 0.0399 _refine_ls_R_factor_gt 0.0367 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0502P)^2^+1.0773P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0987 _refine_ls_wR_factor_ref 0.1008 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4775 _reflns_number_total 5251 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3gc03165a2.cif _cod_data_source_block lcy-64 _cod_depositor_comments 'Adding full bibliography for 7247605--7247608.cif.' _cod_database_code 7247607 _shelx_shelxl_version_number 2017/1 _chemical_oxdiff_formula 'C H O N P Cl' _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. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2.a Secondary CH2 refined with riding coordinates: C26(H26A,H26B) 2.b Aromatic/amide H refined with riding coordinates: C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C14(H14), C15(H15), C16(H16), C17(H17), C29(H29), C30(H30), C32(H32), C33(H33) 2.c Idealised Me refined as rotating group: C23(H23A,H23B,H23C), C25(H25A,H25B,H25C) ; _shelx_res_file ; TITL lcy-64_a.res in P2(1)/c lcy-64.res created by SHELXL-2017/1 at 17:10:29 on 03-Jul-2022 REM Old TITL lcy-64 in P2(1)/c REM SHELXT solution in P2(1)/c REM R1 0.117, Rweak 0.018, Alpha 0.030, Orientation as input REM Formula found by SHELXT: C33 O5 P Cl CELL 1.54184 14.9304 9.0992 21.2031 90 106.572 90 ZERR 4 0.0002 0.0001 0.0003 0 0.002 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H Cl O P UNIT 132 104 4 20 4 L.S. 10 PLAN 8 CONF BOND $H LIST 4 MORE -1 fmap 2 ACTA REM REM REM WGHT 0.050200 1.077300 FVAR 0.41503 CL1 3 0.609391 0.849293 0.589022 11.00000 0.04088 0.05875 = 0.06731 0.00257 0.00427 -0.00838 P1 5 0.194222 0.522697 0.672761 11.00000 0.02385 0.02143 = 0.01922 0.00034 0.00357 0.00027 O1 4 0.236418 0.259085 0.751910 11.00000 0.05113 0.03349 = 0.02413 0.00781 0.00539 -0.00255 O2 4 0.219028 0.094735 0.669940 11.00000 0.07956 0.02289 = 0.04087 0.00554 0.01728 0.00358 O3 4 0.353443 0.180967 0.591082 11.00000 0.02492 0.03720 = 0.04989 -0.00619 0.00229 0.00637 O4 4 0.213185 0.103338 0.529096 11.00000 0.02948 0.02283 = 0.03781 -0.00648 0.00362 0.00185 O5 4 0.214578 0.599121 0.386726 11.00000 0.04468 0.03810 = 0.02512 0.00468 0.01074 0.00461 C1 1 0.125423 0.524416 0.730269 11.00000 0.02913 0.02494 = 0.02183 0.00139 0.00514 -0.00046 C2 1 0.042018 0.445697 0.714534 11.00000 0.03543 0.03598 = 0.02732 -0.00507 0.00812 -0.00765 AFIX 43 H2 2 0.023855 0.391891 0.675667 11.00000 -1.20000 AFIX 0 C3 1 -0.013905 0.447196 0.756454 11.00000 0.03640 0.04017 = 0.04012 -0.00163 0.01557 -0.00921 AFIX 43 H3 2 -0.069489 0.394249 0.745769 11.00000 -1.20000 AFIX 0 C4 1 0.012667 0.527390 0.814341 11.00000 0.04675 0.03434 = 0.03655 0.00180 0.02233 -0.00148 AFIX 43 H4 2 -0.025464 0.529381 0.842190 11.00000 -1.20000 AFIX 0 C5 1 0.095651 0.604226 0.830632 11.00000 0.04709 0.03349 = 0.02647 -0.00400 0.01362 -0.00229 AFIX 43 H5 2 0.113771 0.656842 0.869830 11.00000 -1.20000 AFIX 0 C6 1 0.152508 0.603595 0.788815 11.00000 0.03268 0.03028 = 0.02611 -0.00261 0.00711 -0.00350 AFIX 43 H6 2 0.208361 0.655850 0.799936 11.00000 -1.20000 AFIX 0 C7 1 0.299258 0.625278 0.711729 11.00000 0.02535 0.02607 = 0.02431 -0.00088 0.00572 -0.00064 C8 1 0.304062 0.775620 0.702868 11.00000 0.03191 0.02879 = 0.04546 0.00415 0.00291 -0.00151 AFIX 43 H8 2 0.254485 0.824991 0.674060 11.00000 -1.20000 AFIX 0 C9 1 0.383414 0.851995 0.737303 11.00000 0.04036 0.03145 = 0.06774 -0.00139 0.00690 -0.00997 AFIX 43 H9 2 0.387055 0.952811 0.731255 11.00000 -1.20000 AFIX 0 C10 1 0.456816 0.779649 0.780367 11.00000 0.02836 0.04727 = 0.05297 -0.00919 0.00442 -0.01075 AFIX 43 H10 2 0.509742 0.831665 0.803227 11.00000 -1.20000 AFIX 0 C11 1 0.451939 0.630742 0.789589 11.00000 0.02571 0.04605 = 0.04166 0.00022 0.00035 0.00156 AFIX 43 H11 2 0.501311 0.582372 0.819066 11.00000 -1.20000 AFIX 0 C12 1 0.373814 0.552502 0.755165 11.00000 0.02899 0.03064 = 0.03778 0.00183 0.00332 0.00156 AFIX 43 H12 2 0.371076 0.451481 0.761014 11.00000 -1.20000 AFIX 0 C13 1 0.128442 0.613023 0.599214 11.00000 0.02244 0.02196 = 0.02391 0.00072 0.00350 -0.00014 C14 1 0.067396 0.726788 0.602874 11.00000 0.03186 0.03060 = 0.02736 -0.00164 0.00741 0.00460 AFIX 43 H14 2 0.063699 0.758012 0.643821 11.00000 -1.20000 AFIX 0 C15 1 0.012402 0.793712 0.546661 11.00000 0.02931 0.03044 = 0.03705 0.00267 0.00719 0.01027 AFIX 43 H15 2 -0.027832 0.869797 0.549551 11.00000 -1.20000 AFIX 0 C16 1 0.018098 0.745646 0.485722 11.00000 0.02566 0.03132 = 0.02776 0.00698 0.00172 0.00227 AFIX 43 H16 2 -0.018850 0.789702 0.447568 11.00000 -1.20000 AFIX 0 C17 1 0.077885 0.633450 0.481233 11.00000 0.02603 0.02828 = 0.02290 0.00242 0.00416 -0.00111 AFIX 43 H17 2 0.080585 0.603539 0.439873 11.00000 -1.20000 AFIX 0 C18 1 0.135246 0.562451 0.537632 11.00000 0.02234 0.02289 = 0.02152 0.00139 0.00402 -0.00137 C19 1 0.192086 0.436182 0.531002 11.00000 0.02449 0.02489 = 0.02303 -0.00055 0.00538 0.00040 C20 1 0.220182 0.335231 0.580415 11.00000 0.02212 0.02109 = 0.02548 -0.00154 0.00426 -0.00035 C21 1 0.211428 0.348934 0.646050 11.00000 0.02791 0.02156 = 0.02404 0.00161 0.00401 0.00080 C22 1 0.222626 0.221851 0.688004 11.00000 0.03315 0.02781 = 0.02776 0.00368 0.00555 0.00260 C23 1 0.231148 0.141267 0.795724 11.00000 0.07329 0.05015 = 0.03047 0.01583 0.00665 -0.01304 AFIX 137 H23A 2 0.184429 0.072072 0.773151 11.00000 -1.50000 H23B 2 0.214847 0.180041 0.833095 11.00000 -1.50000 H23C 2 0.290643 0.092887 0.810230 11.00000 -1.50000 AFIX 0 C24 1 0.270687 0.199018 0.568763 11.00000 0.02618 0.02481 = 0.02668 0.00124 0.00503 0.00177 C25 1 0.254428 -0.036360 0.521001 11.00000 0.04694 0.02518 = 0.05748 -0.00930 0.01387 0.00418 AFIX 137 H25A 2 0.299223 -0.022478 0.496824 11.00000 -1.50000 H25B 2 0.206429 -0.102433 0.497344 11.00000 -1.50000 H25C 2 0.285056 -0.077051 0.563453 11.00000 -1.50000 AFIX 0 C26 1 0.213846 0.414644 0.465839 11.00000 0.03516 0.02779 = 0.02558 -0.00128 0.00971 0.00366 AFIX 23 H26A 2 0.156599 0.386869 0.432941 11.00000 -1.20000 H26B 2 0.257142 0.333155 0.470530 11.00000 -1.20000 AFIX 0 C27 1 0.255347 0.547135 0.440255 11.00000 0.03665 0.02996 = 0.02540 -0.00135 0.01428 0.00817 C28 1 0.346468 0.612211 0.478698 11.00000 0.03226 0.03146 = 0.03265 0.00246 0.01391 0.00732 C29 1 0.390304 0.578881 0.544287 11.00000 0.03993 0.06245 = 0.04170 0.01971 0.00503 -0.00937 AFIX 43 H29 2 0.364957 0.507502 0.565519 11.00000 -1.20000 AFIX 0 C30 1 0.471440 0.651162 0.578260 11.00000 0.04417 0.07574 = 0.04359 0.01869 -0.00054 -0.01111 AFIX 43 H30 2 0.499587 0.630758 0.622466 11.00000 -1.20000 AFIX 0 C31 1 0.509874 0.753485 0.545819 11.00000 0.03121 0.04204 = 0.04885 0.00253 0.01061 0.00351 C32 1 0.470451 0.784281 0.480298 11.00000 0.04208 0.04168 = 0.05076 0.00763 0.01838 -0.00113 AFIX 43 H32 2 0.498468 0.850958 0.458584 11.00000 -1.20000 AFIX 0 C33 1 0.388429 0.714257 0.447362 11.00000 0.04146 0.04397 = 0.03455 0.00572 0.01410 0.00113 AFIX 43 H33 2 0.360611 0.735812 0.403229 11.00000 -1.20000 AFIX 0 HKLF 4 REM lcy-64_a.res in P2(1)/c REM R1 = 0.0367 for 4775 Fo > 4sig(Fo) and 0.0399 for all 5251 data REM 363 parameters refined using 0 restraints END WGHT 0.0502 1.0773 REM Highest difference peak 0.312, deepest hole -0.391, 1-sigma level 0.046 Q1 1 0.5721 0.8625 0.6201 11.00000 0.05 0.31 Q2 1 0.1509 0.5149 0.7116 11.00000 0.05 0.28 Q3 1 0.2230 0.4327 0.6592 11.00000 0.05 0.27 Q4 1 0.1743 0.3933 0.6507 11.00000 0.05 0.23 Q5 1 0.1571 0.5636 0.6312 11.00000 0.05 0.23 Q6 1 0.2592 0.5755 0.6997 11.00000 0.05 0.22 Q7 1 0.2366 0.2741 0.5716 11.00000 0.05 0.21 Q8 1 0.2700 0.1681 0.8379 11.00000 0.05 0.20 ; _shelx_res_checksum 9664 _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 2.216 _oxdiff_exptl_absorpt_empirical_full_min 0.586 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.60939(3) 0.84929(7) 0.58902(3) 0.05796(16) Uani 1 1 d . . . . . P1 P 0.19422(2) 0.52270(4) 0.67276(2) 0.02203(11) Uani 1 1 d . . . . . O1 O 0.23642(9) 0.25908(14) 0.75191(5) 0.0374(3) Uani 1 1 d . . . . . O2 O 0.21903(11) 0.09473(14) 0.66994(6) 0.0478(3) Uani 1 1 d . . . . . O3 O 0.35344(8) 0.18097(14) 0.59108(6) 0.0391(3) Uani 1 1 d . . . . . O4 O 0.21318(7) 0.10334(12) 0.52910(5) 0.0313(3) Uani 1 1 d . . . . . O5 O 0.21458(8) 0.59912(14) 0.38673(5) 0.0358(3) Uani 1 1 d . . . . . C1 C 0.12542(10) 0.52442(17) 0.73027(7) 0.0257(3) Uani 1 1 d . . . . . C2 C 0.04202(11) 0.4457(2) 0.71453(8) 0.0331(4) Uani 1 1 d . . . . . H2 H 0.023855 0.391891 0.675667 0.040 Uiso 1 1 calc R U . . . C3 C -0.01391(12) 0.4472(2) 0.75645(9) 0.0379(4) Uani 1 1 d . . . . . H3 H -0.069489 0.394249 0.745769 0.046 Uiso 1 1 calc R U . . . C4 C 0.01267(13) 0.5274(2) 0.81434(8) 0.0371(4) Uani 1 1 d . . . . . H4 H -0.025464 0.529381 0.842190 0.044 Uiso 1 1 calc R U . . . C5 C 0.09565(12) 0.6042(2) 0.83063(8) 0.0350(4) Uani 1 1 d . . . . . H5 H 0.113771 0.656842 0.869830 0.042 Uiso 1 1 calc R U . . . C6 C 0.15251(11) 0.60359(18) 0.78881(7) 0.0300(3) Uani 1 1 d . . . . . H6 H 0.208361 0.655850 0.799936 0.036 Uiso 1 1 calc R U . . . C7 C 0.29926(10) 0.62528(17) 0.71173(7) 0.0255(3) Uani 1 1 d . . . . . C8 C 0.30406(12) 0.7756(2) 0.70287(9) 0.0371(4) Uani 1 1 d . . . . . H8 H 0.254485 0.824991 0.674060 0.044 Uiso 1 1 calc R U . . . C9 C 0.38341(13) 0.8520(2) 0.73730(11) 0.0483(5) Uani 1 1 d . . . . . H9 H 0.387055 0.952811 0.731255 0.058 Uiso 1 1 calc R U . . . C10 C 0.45682(12) 0.7796(2) 0.78037(10) 0.0443(4) Uani 1 1 d . . . . . H10 H 0.509742 0.831665 0.803227 0.053 Uiso 1 1 calc R U . . . C11 C 0.45194(11) 0.6307(2) 0.78959(9) 0.0397(4) Uani 1 1 d . . . . . H11 H 0.501311 0.582372 0.819066 0.048 Uiso 1 1 calc R U . . . C12 C 0.37381(11) 0.5525(2) 0.75517(8) 0.0338(4) Uani 1 1 d . . . . . H12 H 0.371076 0.451481 0.761014 0.041 Uiso 1 1 calc R U . . . C13 C 0.12844(10) 0.61302(16) 0.59921(7) 0.0234(3) Uani 1 1 d . . . . . C14 C 0.06740(11) 0.72679(19) 0.60287(8) 0.0302(3) Uani 1 1 d . . . . . H14 H 0.063699 0.758012 0.643821 0.036 Uiso 1 1 calc R U . . . C15 C 0.01240(11) 0.79371(19) 0.54666(8) 0.0327(4) Uani 1 1 d . . . . . H15 H -0.027832 0.869797 0.549551 0.039 Uiso 1 1 calc R U . . . C16 C 0.01810(10) 0.74565(18) 0.48572(7) 0.0295(3) Uani 1 1 d . . . . . H16 H -0.018850 0.789702 0.447568 0.035 Uiso 1 1 calc R U . . . C17 C 0.07788(10) 0.63345(18) 0.48123(7) 0.0263(3) Uani 1 1 d . . . . . H17 H 0.080585 0.603539 0.439873 0.032 Uiso 1 1 calc R U . . . C18 C 0.13525(9) 0.56245(16) 0.53763(7) 0.0227(3) Uani 1 1 d . . . . . C19 C 0.19209(10) 0.43618(17) 0.53100(7) 0.0244(3) Uani 1 1 d . . . . . C20 C 0.22018(10) 0.33523(16) 0.58041(7) 0.0234(3) Uani 1 1 d . . . . . C21 C 0.21143(10) 0.34893(17) 0.64605(7) 0.0252(3) Uani 1 1 d . . . . . C22 C 0.22263(11) 0.22185(18) 0.68800(8) 0.0302(3) Uani 1 1 d . . . . . C23 C 0.23115(17) 0.1413(2) 0.79572(9) 0.0530(5) Uani 1 1 d . . . . . H23A H 0.184429 0.072072 0.773151 0.079 Uiso 1 1 calc R U . . . H23B H 0.214847 0.180041 0.833095 0.079 Uiso 1 1 calc R U . . . H23C H 0.290643 0.092887 0.810230 0.079 Uiso 1 1 calc R U . . . C24 C 0.27069(10) 0.19902(17) 0.56876(7) 0.0264(3) Uani 1 1 d . . . . . C25 C 0.25443(13) -0.0364(2) 0.52100(10) 0.0434(4) Uani 1 1 d . . . . . H25A H 0.299223 -0.022478 0.496824 0.065 Uiso 1 1 calc R U . . . H25B H 0.206429 -0.102433 0.497344 0.065 Uiso 1 1 calc R U . . . H25C H 0.285056 -0.077051 0.563453 0.065 Uiso 1 1 calc R U . . . C26 C 0.21385(11) 0.41464(18) 0.46584(7) 0.0293(3) Uani 1 1 d . . . . . H26A H 0.156599 0.386869 0.432941 0.035 Uiso 1 1 calc R U . . . H26B H 0.257142 0.333155 0.470530 0.035 Uiso 1 1 calc R U . . . C27 C 0.25535(11) 0.54713(18) 0.44026(7) 0.0295(3) Uani 1 1 d . . . . . C28 C 0.34647(11) 0.61221(19) 0.47870(8) 0.0312(3) Uani 1 1 d . . . . . C29 C 0.39030(13) 0.5789(3) 0.54429(9) 0.0494(5) Uani 1 1 d . . . . . H29 H 0.364957 0.507502 0.565519 0.059 Uiso 1 1 calc R U . . . C30 C 0.47144(14) 0.6512(3) 0.57826(10) 0.0572(6) Uani 1 1 d . . . . . H30 H 0.499587 0.630758 0.622466 0.069 Uiso 1 1 calc R U . . . C31 C 0.50987(12) 0.7535(2) 0.54582(9) 0.0409(4) Uani 1 1 d . . . . . C32 C 0.47045(13) 0.7843(2) 0.48030(10) 0.0438(4) Uani 1 1 d . . . . . H32 H 0.498468 0.850958 0.458584 0.053 Uiso 1 1 calc R U . . . C33 C 0.38843(12) 0.7143(2) 0.44736(9) 0.0393(4) Uani 1 1 d . . . . . H33 H 0.360611 0.735812 0.403229 0.047 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 Cl1 0.0409(3) 0.0587(3) 0.0673(3) 0.0026(3) 0.0043(2) -0.0084(2) P1 0.02385(19) 0.0214(2) 0.01922(18) 0.00034(13) 0.00357(13) 0.00027(14) O1 0.0511(7) 0.0335(7) 0.0241(5) 0.0078(5) 0.0054(5) -0.0026(5) O2 0.0796(10) 0.0229(7) 0.0409(7) 0.0055(5) 0.0173(6) 0.0036(6) O3 0.0249(5) 0.0372(7) 0.0499(7) -0.0062(5) 0.0023(5) 0.0064(5) O4 0.0295(5) 0.0228(6) 0.0378(6) -0.0065(5) 0.0036(4) 0.0019(4) O5 0.0447(6) 0.0381(7) 0.0251(5) 0.0047(5) 0.0107(5) 0.0046(5) C1 0.0291(7) 0.0249(8) 0.0218(7) 0.0014(6) 0.0051(6) -0.0005(6) C2 0.0354(8) 0.0360(9) 0.0273(7) -0.0051(7) 0.0081(6) -0.0077(7) C3 0.0364(9) 0.0402(10) 0.0401(9) -0.0016(8) 0.0156(7) -0.0092(7) C4 0.0468(10) 0.0343(9) 0.0365(9) 0.0018(7) 0.0223(7) -0.0015(8) C5 0.0471(9) 0.0335(9) 0.0265(7) -0.0040(7) 0.0136(7) -0.0023(7) C6 0.0327(8) 0.0303(9) 0.0261(7) -0.0026(6) 0.0071(6) -0.0035(6) C7 0.0254(7) 0.0261(8) 0.0243(7) -0.0009(6) 0.0057(6) -0.0006(6) C8 0.0319(8) 0.0288(9) 0.0455(10) 0.0041(7) 0.0029(7) -0.0015(7) C9 0.0404(10) 0.0314(10) 0.0677(13) -0.0014(9) 0.0069(9) -0.0100(8) C10 0.0284(8) 0.0473(11) 0.0530(11) -0.0092(9) 0.0044(8) -0.0107(8) C11 0.0257(8) 0.0461(11) 0.0417(9) 0.0002(8) 0.0004(7) 0.0016(7) C12 0.0290(8) 0.0306(9) 0.0378(8) 0.0018(7) 0.0033(6) 0.0016(7) C13 0.0224(7) 0.0220(7) 0.0239(7) 0.0007(5) 0.0035(5) -0.0001(6) C14 0.0319(8) 0.0306(9) 0.0274(7) -0.0016(6) 0.0074(6) 0.0046(6) C15 0.0293(8) 0.0304(9) 0.0370(8) 0.0027(7) 0.0072(6) 0.0103(6) C16 0.0257(7) 0.0313(8) 0.0278(7) 0.0070(6) 0.0017(6) 0.0023(6) C17 0.0260(7) 0.0283(8) 0.0229(7) 0.0024(6) 0.0042(6) -0.0011(6) C18 0.0223(7) 0.0229(7) 0.0215(6) 0.0014(6) 0.0040(5) -0.0014(6) C19 0.0245(7) 0.0249(8) 0.0230(7) -0.0006(6) 0.0054(5) 0.0004(6) C20 0.0221(7) 0.0211(7) 0.0255(7) -0.0015(6) 0.0043(5) -0.0004(5) C21 0.0279(7) 0.0216(8) 0.0240(7) 0.0016(6) 0.0040(5) 0.0008(6) C22 0.0332(8) 0.0278(9) 0.0278(7) 0.0037(6) 0.0056(6) 0.0026(6) C23 0.0733(14) 0.0501(12) 0.0305(9) 0.0158(8) 0.0066(9) -0.0130(10) C24 0.0262(7) 0.0248(8) 0.0267(7) 0.0012(6) 0.0050(6) 0.0018(6) C25 0.0469(10) 0.0252(9) 0.0575(11) -0.0093(8) 0.0139(9) 0.0042(7) C26 0.0352(8) 0.0278(8) 0.0256(7) -0.0013(6) 0.0097(6) 0.0037(6) C27 0.0367(8) 0.0300(9) 0.0254(7) -0.0013(6) 0.0143(6) 0.0082(7) C28 0.0323(8) 0.0315(9) 0.0327(8) 0.0025(7) 0.0139(6) 0.0073(7) C29 0.0399(10) 0.0625(14) 0.0417(10) 0.0197(9) 0.0050(8) -0.0094(9) C30 0.0442(11) 0.0757(16) 0.0436(10) 0.0187(11) -0.0005(8) -0.0111(10) C31 0.0312(8) 0.0420(11) 0.0489(10) 0.0025(8) 0.0106(7) 0.0035(7) C32 0.0421(10) 0.0417(11) 0.0508(11) 0.0076(9) 0.0184(8) -0.0011(8) C33 0.0415(9) 0.0440(11) 0.0346(9) 0.0057(8) 0.0141(7) 0.0011(8) 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' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.2955 0.4335 '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 C1 P1 C7 105.86(7) . . ? C13 P1 C1 107.96(7) . . ? C13 P1 C7 110.49(7) . . ? C21 P1 C1 113.39(7) . . ? C21 P1 C7 115.62(7) . . ? C21 P1 C13 103.38(7) . . ? C22 O1 C23 116.10(14) . . ? C24 O4 C25 115.38(12) . . ? C2 C1 P1 118.44(11) . . ? C6 C1 P1 122.04(12) . . ? C6 C1 C2 119.51(14) . . ? C1 C2 H2 119.9 . . ? C3 C2 C1 120.26(15) . . ? C3 C2 H2 119.9 . . ? C2 C3 H3 119.9 . . ? C2 C3 C4 120.14(16) . . ? C4 C3 H3 119.9 . . ? C3 C4 H4 120.0 . . ? C5 C4 C3 119.95(16) . . ? C5 C4 H4 120.0 . . ? C4 C5 H5 119.8 . . ? C4 C5 C6 120.43(15) . . ? C6 C5 H5 119.8 . . ? C1 C6 H6 120.1 . . ? C5 C6 C1 119.71(15) . . ? C5 C6 H6 120.1 . . ? C8 C7 P1 121.27(12) . . ? C8 C7 C12 119.77(14) . . ? C12 C7 P1 118.79(12) . . ? C7 C8 H8 120.2 . . ? C7 C8 C9 119.51(16) . . ? C9 C8 H8 120.2 . . ? C8 C9 H9 119.7 . . ? C10 C9 C8 120.52(18) . . ? C10 C9 H9 119.7 . . ? C9 C10 H10 120.0 . . ? C11 C10 C9 120.08(16) . . ? C11 C10 H10 120.0 . . ? C10 C11 H11 119.9 . . ? C10 C11 C12 120.22(16) . . ? C12 C11 H11 119.9 . . ? C7 C12 H12 120.0 . . ? C11 C12 C7 119.90(16) . . ? C11 C12 H12 120.0 . . ? C14 C13 P1 119.82(11) . . ? C14 C13 C18 120.81(13) . . ? C18 C13 P1 119.28(11) . . ? C13 C14 H14 119.5 . . ? C15 C14 C13 121.06(14) . . ? C15 C14 H14 119.5 . . ? C14 C15 H15 120.5 . . ? C14 C15 C16 118.99(15) . . ? C16 C15 H15 120.5 . . ? C15 C16 H16 119.7 . . ? C17 C16 C15 120.69(14) . . ? C17 C16 H16 119.7 . . ? C16 C17 H17 119.0 . . ? C16 C17 C18 121.92(14) . . ? C18 C17 H17 119.0 . . ? C13 C18 C19 122.81(12) . . ? C17 C18 C13 116.52(13) . . ? C17 C18 C19 120.49(13) . . ? C18 C19 C26 118.06(13) . . ? C20 C19 C18 121.03(13) . . ? C20 C19 C26 120.80(14) . . ? C19 C20 C21 126.18(14) . . ? C19 C20 C24 119.06(13) . . ? C21 C20 C24 114.66(13) . . ? C20 C21 P1 117.40(11) . . ? C22 C21 P1 122.41(12) . . ? C22 C21 C20 120.08(14) . . ? O1 C22 C21 112.03(14) . . ? O2 C22 O1 122.28(15) . . ? O2 C22 C21 125.68(15) . . ? O1 C23 H23A 109.5 . . ? O1 C23 H23B 109.5 . . ? O1 C23 H23C 109.5 . . ? H23A C23 H23B 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? O3 C24 O4 124.19(14) . . ? O3 C24 C20 123.65(14) . . ? O4 C24 C20 112.13(12) . . ? O4 C25 H25A 109.5 . . ? O4 C25 H25B 109.5 . . ? O4 C25 H25C 109.5 . . ? H25A C25 H25B 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C19 C26 H26A 108.3 . . ? C19 C26 H26B 108.3 . . ? C19 C26 C27 115.83(13) . . ? H26A C26 H26B 107.4 . . ? C27 C26 H26A 108.3 . . ? C27 C26 H26B 108.3 . . ? O5 C27 C26 119.48(15) . . ? O5 C27 C28 119.26(15) . . ? C28 C27 C26 121.23(13) . . ? C29 C28 C27 123.67(16) . . ? C33 C28 C27 117.91(15) . . ? C33 C28 C29 118.40(17) . . ? C28 C29 H29 119.7 . . ? C30 C29 C28 120.55(18) . . ? C30 C29 H29 119.7 . . ? C29 C30 H30 120.4 . . ? C31 C30 C29 119.24(18) . . ? C31 C30 H30 120.4 . . ? C30 C31 Cl1 119.39(15) . . ? C32 C31 Cl1 119.02(15) . . ? C32 C31 C30 121.58(18) . . ? C31 C32 H32 120.7 . . ? C31 C32 C33 118.66(18) . . ? C33 C32 H32 120.7 . . ? C28 C33 H33 119.3 . . ? C32 C33 C28 121.47(17) . . ? C32 C33 H33 119.3 . . ? 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 Cl1 C31 1.7408(19) . ? P1 C1 1.8046(16) . ? P1 C7 1.8095(15) . ? P1 C13 1.7884(14) . ? P1 C21 1.7233(16) . ? O1 C22 1.354(2) . ? O1 C23 1.435(2) . ? O2 C22 1.215(2) . ? O3 C24 1.2017(18) . ? O4 C24 1.3381(18) . ? O4 C25 1.444(2) . ? O5 C27 1.2200(19) . ? C1 C2 1.392(2) . ? C1 C6 1.392(2) . ? C2 H2 0.9300 . ? C2 C3 1.382(2) . ? C3 H3 0.9300 . ? C3 C4 1.385(3) . ? C4 H4 0.9300 . ? C4 C5 1.378(2) . ? C5 H5 0.9300 . ? C5 C6 1.391(2) . ? C6 H6 0.9300 . ? C7 C8 1.385(2) . ? C7 C12 1.393(2) . ? C8 H8 0.9300 . ? C8 C9 1.388(2) . ? C9 H9 0.9300 . ? C9 C10 1.377(3) . ? C10 H10 0.9300 . ? C10 C11 1.374(3) . ? C11 H11 0.9300 . ? C11 C12 1.384(2) . ? C12 H12 0.9300 . ? C13 C14 1.396(2) . ? C13 C18 1.415(2) . ? C14 H14 0.9300 . ? C14 C15 1.381(2) . ? C15 H15 0.9300 . ? C15 C16 1.390(2) . ? C16 H16 0.9300 . ? C16 C17 1.377(2) . ? C17 H17 0.9300 . ? C17 C18 1.413(2) . ? C18 C19 1.459(2) . ? C19 C20 1.366(2) . ? C19 C26 1.520(2) . ? C20 C21 1.440(2) . ? C20 C24 1.507(2) . ? C21 C22 1.439(2) . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? C26 C27 1.524(2) . ? C27 C28 1.494(2) . ? C28 C29 1.391(2) . ? C28 C33 1.391(2) . ? C29 H29 0.9300 . ? C29 C30 1.386(3) . ? C30 H30 0.9300 . ? C30 C31 1.376(3) . ? C31 C32 1.374(3) . ? C32 H32 0.9300 . ? C32 C33 1.380(3) . ? C33 H33 0.9300 . ? 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 Cl1 C31 C32 C33 -176.17(15) . . . . ? P1 C1 C2 C3 -178.36(14) . . . . ? P1 C1 C6 C5 178.34(13) . . . . ? P1 C7 C8 C9 175.40(15) . . . . ? P1 C7 C12 C11 -174.84(13) . . . . ? P1 C13 C14 C15 -176.85(13) . . . . ? P1 C13 C18 C17 176.81(11) . . . . ? P1 C13 C18 C19 1.7(2) . . . . ? P1 C21 C22 O1 -12.17(19) . . . . ? P1 C21 C22 O2 166.67(15) . . . . ? O5 C27 C28 C29 168.40(18) . . . . ? O5 C27 C28 C33 -10.1(2) . . . . ? C1 P1 C7 C8 -90.19(15) . . . . ? C1 P1 C7 C12 85.05(14) . . . . ? C1 P1 C13 C14 31.49(14) . . . . ? C1 P1 C13 C18 -145.03(12) . . . . ? C1 P1 C21 C20 148.83(11) . . . . ? C1 P1 C21 C22 -34.94(15) . . . . ? C1 C2 C3 C4 0.1(3) . . . . ? C2 C1 C6 C5 -0.5(2) . . . . ? C2 C3 C4 C5 -0.9(3) . . . . ? C3 C4 C5 C6 0.9(3) . . . . ? C4 C5 C6 C1 -0.2(3) . . . . ? C6 C1 C2 C3 0.6(3) . . . . ? C7 P1 C1 C2 -176.45(13) . . . . ? C7 P1 C1 C6 4.65(15) . . . . ? C7 P1 C13 C14 -83.83(14) . . . . ? C7 P1 C13 C18 99.65(13) . . . . ? C7 P1 C21 C20 -88.66(12) . . . . ? C7 P1 C21 C22 87.57(14) . . . . ? C7 C8 C9 C10 -0.4(3) . . . . ? C8 C7 C12 C11 0.5(3) . . . . ? C8 C9 C10 C11 0.0(3) . . . . ? C9 C10 C11 C12 0.7(3) . . . . ? C10 C11 C12 C7 -0.9(3) . . . . ? C12 C7 C8 C9 0.2(3) . . . . ? C13 P1 C1 C2 65.22(14) . . . . ? C13 P1 C1 C6 -113.68(13) . . . . ? C13 P1 C7 C8 26.44(16) . . . . ? C13 P1 C7 C12 -158.31(12) . . . . ? C13 P1 C21 C20 32.20(13) . . . . ? C13 P1 C21 C22 -151.57(13) . . . . ? C13 C14 C15 C16 0.4(3) . . . . ? C13 C18 C19 C20 19.0(2) . . . . ? C13 C18 C19 C26 -164.95(14) . . . . ? C14 C13 C18 C17 0.3(2) . . . . ? C14 C13 C18 C19 -174.78(14) . . . . ? C14 C15 C16 C17 -0.3(3) . . . . ? C15 C16 C17 C18 0.2(2) . . . . ? C16 C17 C18 C13 -0.3(2) . . . . ? C16 C17 C18 C19 174.97(14) . . . . ? C17 C18 C19 C20 -155.93(14) . . . . ? C17 C18 C19 C26 20.1(2) . . . . ? C18 C13 C14 C15 -0.4(2) . . . . ? C18 C19 C20 C21 -10.0(2) . . . . ? C18 C19 C20 C24 174.05(13) . . . . ? C18 C19 C26 C27 52.21(18) . . . . ? C19 C20 C21 P1 -18.8(2) . . . . ? C19 C20 C21 C22 164.90(15) . . . . ? C19 C20 C24 O3 104.41(18) . . . . ? C19 C20 C24 O4 -73.56(17) . . . . ? C19 C26 C27 O5 -120.88(16) . . . . ? C19 C26 C27 C28 60.80(19) . . . . ? C20 C19 C26 C27 -131.72(15) . . . . ? C20 C21 C22 O1 163.96(13) . . . . ? C20 C21 C22 O2 -17.2(3) . . . . ? C21 P1 C1 C2 -48.68(15) . . . . ? C21 P1 C1 C6 132.42(13) . . . . ? C21 P1 C7 C8 143.38(14) . . . . ? C21 P1 C7 C12 -41.37(15) . . . . ? C21 P1 C13 C14 151.89(13) . . . . ? C21 P1 C13 C18 -24.63(13) . . . . ? C21 C20 C24 O3 -72.0(2) . . . . ? C21 C20 C24 O4 109.99(15) . . . . ? C23 O1 C22 O2 -10.0(2) . . . . ? C23 O1 C22 C21 168.91(16) . . . . ? C24 C20 C21 P1 157.37(11) . . . . ? C24 C20 C21 C22 -19.0(2) . . . . ? C25 O4 C24 O3 8.2(2) . . . . ? C25 O4 C24 C20 -173.88(14) . . . . ? C26 C19 C20 C21 174.08(14) . . . . ? C26 C19 C20 C24 -1.9(2) . . . . ? C26 C27 C28 C29 -13.3(2) . . . . ? C26 C27 C28 C33 168.25(15) . . . . ? C27 C28 C29 C30 -175.4(2) . . . . ? C27 C28 C33 C32 177.06(17) . . . . ? C28 C29 C30 C31 -1.9(4) . . . . ? C29 C28 C33 C32 -1.5(3) . . . . ? C29 C30 C31 Cl1 177.70(18) . . . . ? C29 C30 C31 C32 -0.9(4) . . . . ? C30 C31 C32 C33 2.4(3) . . . . ? C31 C32 C33 C28 -1.2(3) . . . . ? C33 C28 C29 C30 3.1(3) . . . . ?