#------------------------------------------------------------------------------ #$Date: 2019-05-18 06:54:06 +0300 (Sat, 18 May 2019) $ #$Revision: 215298 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/68/7156870.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_7156870 loop_ _publ_author_name 'Boureghda, Chaima' 'Mac\'e, aur\'elie' 'Berr\'ee, Fabienne' 'Roisnel, Thierry' 'Debache, Adbelmadjid' 'Carboni, Bertrand' _publ_section_title ; Ene reactions of 2-borylated \a-methylstyrenes: a practical route to 4-methylenechromanes and derivatives ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/C9OB00963A _journal_year 2019 _chemical_compound_source 'synthesis as described' _chemical_formula_moiety 'C31 H30 N O3 P' _chemical_formula_sum 'C31 H30 N O3 P' _chemical_formula_weight 495.53 _chemical_name_systematic ; ? ; _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _audit_update_record ; 2019-04-04 deposited with the CCDC. 2019-05-17 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90.278(5) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 9.1640(12) _cell_length_b 10.0512(13) _cell_length_c 28.621(4) _cell_measurement_reflns_used 8368 _cell_measurement_temperature 150 _cell_measurement_theta_max 27.44 _cell_measurement_theta_min 2.48 _cell_measurement_wavelength 0.71073 _cell_volume 2636.2(6) _computing_cell_refinement 'APEX3 (Bruker, 2015); SAINT (Bruker, 2014)' _computing_data_collection 'SAINT (Bruker, 2014)' _computing_data_reduction 'SAINT (Bruker, 2014)' _computing_molecular_graphics 'SXGRAPH (Farrugia, 1999), Mercury (CSD, 2016)' _computing_publication_material 'CRYSCALC (T. Roisnel, local program, 2017)' _computing_structure_refinement 'SHELXL-2017/1 (Sheldrick, 2017)' _computing_structure_solution 'SHELXT (Sheldrick, 2015)' _diffrn_ambient_temperature 150 _diffrn_detector '(CMOS) PHOTON 100' _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.981 _diffrn_measurement_device_type 'D8 VENTURE Bruker AXS' _diffrn_measurement_method 'rotation images' _diffrn_radiation_monochromator 'multilayer monochromator' _diffrn_radiation_probe x-ray _diffrn_radiation_source 'Incoatec microfocus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0641 _diffrn_reflns_av_unetI/netI 0.0541 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_limit_l_min -37 _diffrn_reflns_number 24887 _diffrn_reflns_theta_full 25.000 _diffrn_reflns_theta_max 27.478 _diffrn_reflns_theta_min 3.008 _exptl_absorpt_coefficient_mu 0.137 _exptl_absorpt_correction_T_max 0.986 _exptl_absorpt_correction_T_min 0.771 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA] ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.249 _exptl_crystal_description prism _exptl_crystal_F_000 1048 _exptl_crystal_size_max 0.180 _exptl_crystal_size_mid 0.130 _exptl_crystal_size_min 0.100 _refine_diff_density_max 1.001 _refine_diff_density_min -0.650 _refine_diff_density_rms 0.086 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.172 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 328 _refine_ls_number_reflns 5846 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.172 _refine_ls_R_factor_all 0.1164 _refine_ls_R_factor_gt 0.1019 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0111P)^2^+12.3888P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2171 _refine_ls_wR_factor_ref 0.2239 _reflns_Friedel_coverage 0.000 _reflns_number_gt 5013 _reflns_number_total 5846 _reflns_threshold_expression >2sigma(I) _cod_data_source_file c9ob00963a2.cif _cod_data_source_block CB223A _cod_database_code 7156870 _shelx_res_file ; TITL import_a.res in P2(1)/n job.res created by SHELXL-2017/1 at 14:06:37 on 21-Nov-2017 CELL 0.71073 9.1640 10.0512 28.6209 90.000 90.278 90.000 ZERR 4.00 0.0012 0.0013 0.0040 0.000 0.005 0.000 LATT 1 SYMM 1/2 - X, 1/2 + Y, 1/2 - Z SFAC C H N O P UNIT 124 120 4 12 4 MERG 2 TWIN -1.00 0.00 0.00 0.00 -1.00 0.00 0.03 0.00 1.00 2 FMAP 2 PLAN 40 ACTA 50.00 BOND $H CONF LIST 4 WPDB -2 L.S. 4 TEMP -123.00 WGHT 0.011100 12.388801 BASF 0.18510 FVAR 0.85347 P1 5 0.383184 0.656005 0.602549 11.00000 0.01665 0.01901 = 0.02471 -0.00025 -0.00042 0.00167 C1 1 0.572676 0.697920 0.593200 11.00000 0.01676 0.02508 = 0.02997 0.00384 -0.00162 -0.00029 C2 1 0.659185 0.615162 0.567377 11.00000 0.02331 0.02884 = 0.03322 -0.00100 -0.00132 0.00045 AFIX 43 H2 2 0.621266 0.533715 0.555646 11.00000 -1.20000 AFIX 0 C3 1 0.803691 0.651149 0.558355 11.00000 0.02188 0.04411 = 0.04160 -0.00092 0.00186 0.00584 AFIX 43 H3 2 0.865109 0.593425 0.541012 11.00000 -1.20000 AFIX 0 C4 1 0.857125 0.772038 0.574922 11.00000 0.02049 0.03751 = 0.04704 -0.00031 0.00323 -0.00163 AFIX 43 H4 2 0.954760 0.797207 0.568263 11.00000 -1.20000 AFIX 0 C5 1 0.770410 0.855270 0.600758 11.00000 0.03210 0.04374 = 0.06013 -0.01044 0.00063 -0.01413 AFIX 43 H5 2 0.807501 0.937513 0.612064 11.00000 -1.20000 AFIX 0 C6 1 0.626608 0.817345 0.610221 11.00000 0.02892 0.02945 = 0.05589 -0.00862 0.00407 -0.00085 AFIX 43 H6 2 0.565820 0.873616 0.628359 11.00000 -1.20000 AFIX 0 C7 1 0.281957 0.740208 0.556511 11.00000 0.01792 0.01668 = 0.02082 -0.00147 0.00190 0.00074 C8 1 0.207358 0.662018 0.523714 11.00000 0.02788 0.02625 = 0.02601 -0.00289 -0.00097 -0.00375 AFIX 43 H8 2 0.206535 0.567935 0.526875 11.00000 -1.20000 AFIX 0 C9 1 0.134900 0.721439 0.486745 11.00000 0.02901 0.03632 = 0.02538 -0.00127 -0.00618 -0.00792 AFIX 43 H9 2 0.084970 0.668280 0.464359 11.00000 -1.20000 AFIX 0 C10 1 0.135275 0.859283 0.482401 11.00000 0.03547 0.03824 = 0.02647 0.00674 -0.00741 0.01111 AFIX 43 H10 2 0.083533 0.900451 0.457455 11.00000 -1.20000 AFIX 0 C11 1 0.210531 0.936068 0.514206 11.00000 0.03310 0.02077 = 0.03345 0.00321 -0.00211 0.00371 AFIX 43 H11 2 0.211451 1.030097 0.510857 11.00000 -1.20000 AFIX 0 C12 1 0.284775 0.877529 0.550974 11.00000 0.02421 0.01346 = 0.02606 -0.00234 -0.00147 0.00287 AFIX 43 H12 2 0.337764 0.931190 0.572476 11.00000 -1.20000 AFIX 0 C13 1 0.334557 0.731594 0.657504 11.00000 0.02702 0.02198 = 0.02393 0.00066 -0.00298 -0.00475 C14 1 0.222367 0.821863 0.663106 11.00000 0.03901 0.02971 = 0.03248 -0.00691 0.00222 0.00282 AFIX 43 H14 2 0.164082 0.846371 0.636950 11.00000 -1.20000 AFIX 0 C15 1 0.193797 0.877346 0.706719 11.00000 0.05233 0.05254 = 0.04230 -0.02075 0.01503 0.00037 AFIX 43 H15 2 0.117774 0.940709 0.710355 11.00000 -1.20000 AFIX 0 C16 1 0.278549 0.838428 0.744982 11.00000 0.07057 0.07151 = 0.02715 -0.01790 0.01196 -0.02271 AFIX 43 H16 2 0.259425 0.874778 0.774974 11.00000 -1.20000 AFIX 0 C17 1 0.390027 0.747422 0.739524 11.00000 0.05228 0.09602 = 0.02647 -0.00106 -0.00801 -0.01280 AFIX 43 H17 2 0.447501 0.721475 0.765691 11.00000 -1.20000 AFIX 0 C18 1 0.417553 0.694843 0.696572 11.00000 0.03760 0.04793 = 0.03128 0.00422 -0.00163 0.00657 AFIX 43 H18 2 0.494369 0.632200 0.693104 11.00000 -1.20000 AFIX 0 N21 3 0.375704 0.499636 0.600273 11.00000 0.01780 0.02393 = 0.03268 -0.00003 -0.00019 0.00308 C22 1 0.254859 0.419291 0.608895 11.00000 0.02289 0.02288 = 0.01916 -0.00199 -0.00323 0.00111 C23 1 0.115556 0.466567 0.621285 11.00000 0.02402 0.01627 = 0.03240 -0.00124 -0.00220 0.00080 AFIX 43 H23 2 0.099454 0.559809 0.622970 11.00000 -1.20000 AFIX 0 C24 1 0.001750 0.380951 0.631051 11.00000 0.01953 0.02782 = 0.02725 -0.00492 -0.00097 -0.00092 AFIX 43 H24 2 -0.090694 0.416037 0.639500 11.00000 -1.20000 AFIX 0 C25 1 0.021157 0.244416 0.628640 11.00000 0.03018 0.02864 = 0.02495 -0.00104 0.00129 -0.00545 AFIX 43 H25 2 -0.056252 0.185372 0.636102 11.00000 -1.20000 AFIX 0 C26 1 0.155718 0.196069 0.615129 11.00000 0.03723 0.01919 = 0.02940 -0.00105 0.00416 0.00305 AFIX 43 H26 2 0.169905 0.102570 0.613437 11.00000 -1.20000 AFIX 0 C27 1 0.269901 0.279288 0.604040 11.00000 0.02530 0.02818 = 0.01723 0.00090 -0.00147 -0.00069 C28 1 0.412743 0.223105 0.589572 11.00000 0.03471 0.01337 = 0.03541 0.00308 0.00433 0.00040 C29 1 0.455037 0.221893 0.545304 11.00000 0.04098 0.03592 = 0.04293 -0.00641 0.01542 0.00014 AFIX 93 H29A 2 0.393295 0.257696 0.521695 11.00000 -1.20000 H29B 2 0.547061 0.185222 0.537217 11.00000 -1.20000 AFIX 0 C30 1 0.506092 0.163923 0.628407 11.00000 0.03894 0.04355 = 0.05547 0.02246 0.01028 0.01918 AFIX 23 H30A 2 0.595375 0.124265 0.614933 11.00000 -1.20000 H30B 2 0.451145 0.092535 0.644397 11.00000 -1.20000 AFIX 0 C31 1 0.549181 0.274152 0.664463 11.00000 0.02594 0.10938 = 0.04379 0.03676 -0.01109 -0.01458 AFIX 13 H31 2 0.458820 0.305845 0.680441 11.00000 -1.20000 AFIX 0 O32 4 0.619354 0.380632 0.646188 11.00000 0.04675 0.06810 = 0.07267 0.02223 -0.02126 -0.00207 AFIX 147 H32 2 0.570687 0.411136 0.623666 11.00000 -1.50000 AFIX 0 C33 1 0.648036 0.203495 0.700917 11.00000 0.02534 0.14050 = 0.09196 0.07373 -0.01025 -0.00363 O34 4 0.770633 0.231339 0.706984 11.00000 0.04144 0.26526 = 0.10542 0.12012 0.00144 0.01133 O35 4 0.570535 0.128934 0.727714 11.00000 0.06689 0.14243 = 0.07321 0.06814 -0.01831 -0.02154 C36 1 0.655510 0.051143 0.764430 11.00000 0.12694 0.14230 = 0.04944 0.05808 -0.03894 -0.05201 AFIX 23 H36A 2 0.602367 -0.030257 0.773822 11.00000 -1.20000 H36B 2 0.753352 0.026028 0.752865 11.00000 -1.20000 AFIX 0 C37 1 0.666034 0.144047 0.802566 11.00000 0.07498 0.08780 = 0.08329 0.04322 -0.01144 0.00087 AFIX 137 H37A 2 0.721396 0.222395 0.792593 11.00000 -1.50000 H37B 2 0.716001 0.101706 0.829013 11.00000 -1.50000 H37C 2 0.567873 0.171299 0.812058 11.00000 -1.50000 AFIX 0 HKLF 4 REM import_a.res in P2(1)/n REM R1 = 0.1019 for 5013 Fo > 4sig(Fo) and 0.1164 for all 5846 data REM 328 parameters refined using 0 restraints END WGHT 0.0113 12.3941 REM Highest difference peak 1.001, deepest hole -0.650, 1-sigma level 0.086 Q1 1 0.7526 0.0669 0.6798 11.00000 0.05 1.00 Q2 1 0.5236 0.3635 0.6666 11.00000 0.05 0.84 Q3 1 0.6072 0.2173 0.6429 11.00000 0.05 0.52 Q4 1 0.3807 0.5771 0.6049 11.00000 0.05 0.46 Q5 1 0.6612 0.1852 0.7331 11.00000 0.05 0.45 Q6 1 0.4876 0.6814 0.6002 11.00000 0.05 0.42 Q7 1 0.7209 -0.0246 0.7654 11.00000 0.05 0.41 Q8 1 0.4961 0.8804 0.5844 11.00000 0.05 0.36 Q9 1 0.5098 0.1633 0.6607 11.00000 0.05 0.35 Q10 1 0.2983 0.7390 0.7391 11.00000 0.05 0.35 Q11 1 0.2653 0.3489 0.6039 11.00000 0.05 0.35 Q12 1 0.6856 0.2751 0.7324 11.00000 0.05 0.34 Q13 1 0.5819 0.8154 0.7305 11.00000 0.05 0.29 Q14 1 0.6215 0.6370 0.5989 11.00000 0.05 0.29 Q15 1 0.5859 0.2026 0.7494 11.00000 0.05 0.29 Q16 1 0.6171 0.7401 0.6085 11.00000 0.05 0.28 Q17 1 0.8240 0.7752 0.6017 11.00000 0.05 0.28 Q18 1 0.2382 0.8043 0.5596 11.00000 0.05 0.28 Q19 1 -0.0087 0.9447 0.4748 11.00000 0.05 0.27 Q20 1 0.4448 0.2430 0.4678 11.00000 0.05 0.27 Q21 1 0.3067 0.8063 0.6571 11.00000 0.05 0.27 Q22 1 0.4511 0.6749 0.7571 11.00000 0.05 0.27 Q23 1 0.5560 0.3185 0.5022 11.00000 0.05 0.26 Q24 1 0.3547 0.2648 0.6060 11.00000 0.05 0.26 Q25 1 0.7796 0.6314 0.5991 11.00000 0.05 0.26 Q26 1 0.7219 0.3927 0.6755 11.00000 0.05 0.26 Q27 1 0.4924 0.0382 0.7927 11.00000 0.05 0.26 Q28 1 0.4576 0.2027 0.6172 11.00000 0.05 0.25 Q29 1 0.8450 0.4786 0.5168 11.00000 0.05 0.25 Q30 1 0.5670 0.1885 0.7588 11.00000 0.05 0.25 Q31 1 0.6471 0.0153 0.7320 11.00000 0.05 0.25 Q32 1 0.6289 0.5258 0.5710 11.00000 0.05 0.25 Q33 1 0.2128 0.6860 0.4904 11.00000 0.05 0.24 Q34 1 0.5383 0.1907 0.8517 11.00000 0.05 0.24 Q35 1 0.4821 0.4942 0.5992 11.00000 0.05 0.24 Q36 1 0.4073 0.0825 0.6497 11.00000 0.05 0.24 Q37 1 0.1024 0.7480 0.7403 11.00000 0.05 0.24 Q38 1 0.7554 0.1909 0.6083 11.00000 0.05 0.24 Q39 1 0.6699 0.3961 0.5600 11.00000 0.05 0.24 Q40 1 0.1823 0.4487 0.6028 11.00000 0.05 0.23 ; _shelx_res_checksum 69777 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' loop_ _atom_site_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 P1 P 0.38318(13) 0.65601(11) 0.60255(4) 0.0201(3) Uani 1 1 d . . C1 C 0.5727(5) 0.6979(5) 0.59320(18) 0.0239(10) Uani 1 1 d . . C2 C 0.6592(5) 0.6152(5) 0.56738(19) 0.0285(11) Uani 1 1 d . . H2 H 0.621266 0.533715 0.555646 0.034 Uiso 1 1 calc R U C3 C 0.8037(6) 0.6511(6) 0.5584(2) 0.0359(12) Uani 1 1 d . . H3 H 0.865109 0.593425 0.541012 0.043 Uiso 1 1 calc R U C4 C 0.8571(6) 0.7720(6) 0.5749(2) 0.0350(12) Uani 1 1 d . . H4 H 0.954760 0.797207 0.568263 0.042 Uiso 1 1 calc R U C5 C 0.7704(6) 0.8553(6) 0.6008(3) 0.0453(15) Uani 1 1 d . . H5 H 0.807501 0.937513 0.612064 0.054 Uiso 1 1 calc R U C6 C 0.6266(6) 0.8173(5) 0.6102(2) 0.0381(13) Uani 1 1 d . . H6 H 0.565820 0.873616 0.628359 0.046 Uiso 1 1 calc R U C7 C 0.2820(5) 0.7402(4) 0.55651(16) 0.0185(9) Uani 1 1 d . . C8 C 0.2074(5) 0.6620(5) 0.52371(17) 0.0267(10) Uani 1 1 d . . H8 H 0.206535 0.567935 0.526875 0.032 Uiso 1 1 calc R U C9 C 0.1349(6) 0.7214(5) 0.48674(18) 0.0303(11) Uani 1 1 d . . H9 H 0.084970 0.668280 0.464359 0.036 Uiso 1 1 calc R U C10 C 0.1353(6) 0.8593(5) 0.48240(19) 0.0334(12) Uani 1 1 d . . H10 H 0.083533 0.900451 0.457455 0.040 Uiso 1 1 calc R U C11 C 0.2105(6) 0.9361(5) 0.51421(19) 0.0291(11) Uani 1 1 d . . H11 H 0.211451 1.030097 0.510857 0.035 Uiso 1 1 calc R U C12 C 0.2848(5) 0.8775(4) 0.55097(17) 0.0212(9) Uani 1 1 d . . H12 H 0.337764 0.931190 0.572476 0.025 Uiso 1 1 calc R U C13 C 0.3346(5) 0.7316(5) 0.65750(17) 0.0243(10) Uani 1 1 d . . C14 C 0.2224(6) 0.8219(5) 0.6631(2) 0.0337(12) Uani 1 1 d . . H14 H 0.164082 0.846371 0.636950 0.040 Uiso 1 1 calc R U C15 C 0.1938(8) 0.8773(7) 0.7067(2) 0.0490(17) Uani 1 1 d . . H15 H 0.117774 0.940709 0.710355 0.059 Uiso 1 1 calc R U C16 C 0.2785(9) 0.8384(8) 0.7450(2) 0.056(2) Uani 1 1 d . . H16 H 0.259425 0.874778 0.774974 0.068 Uiso 1 1 calc R U C17 C 0.3900(9) 0.7474(8) 0.7395(2) 0.058(2) Uani 1 1 d . . H17 H 0.447501 0.721475 0.765691 0.070 Uiso 1 1 calc R U C18 C 0.4176(7) 0.6948(6) 0.6966(2) 0.0389(13) Uani 1 1 d . . H18 H 0.494369 0.632200 0.693104 0.047 Uiso 1 1 calc R U N21 N 0.3757(4) 0.4996(4) 0.60027(15) 0.0248(8) Uani 1 1 d . . C22 C 0.2549(5) 0.4193(5) 0.60890(16) 0.0217(9) Uani 1 1 d . . C23 C 0.1156(5) 0.4666(4) 0.62129(17) 0.0242(10) Uani 1 1 d . . H23 H 0.099454 0.559809 0.622970 0.029 Uiso 1 1 calc R U C24 C 0.0017(5) 0.3810(5) 0.63105(18) 0.0249(10) Uani 1 1 d . . H24 H -0.090694 0.416037 0.639500 0.030 Uiso 1 1 calc R U C25 C 0.0212(6) 0.2444(5) 0.62864(18) 0.0279(11) Uani 1 1 d . . H25 H -0.056252 0.185372 0.636102 0.034 Uiso 1 1 calc R U C26 C 0.1557(6) 0.1961(5) 0.61513(18) 0.0286(11) Uani 1 1 d . . H26 H 0.169905 0.102570 0.613437 0.034 Uiso 1 1 calc R U C27 C 0.2699(5) 0.2793(5) 0.60404(16) 0.0236(10) Uani 1 1 d . . C28 C 0.4127(6) 0.2231(4) 0.58957(19) 0.0278(11) Uani 1 1 d . . C29 C 0.4550(7) 0.2219(6) 0.5453(2) 0.0399(14) Uani 1 1 d . . H29A H 0.393295 0.257696 0.521695 0.048 Uiso 1 1 calc R U H29B H 0.547061 0.185222 0.537217 0.048 Uiso 1 1 calc R U C30 C 0.5061(7) 0.1639(6) 0.6284(2) 0.0460(16) Uani 1 1 d . . H30A H 0.595375 0.124265 0.614933 0.055 Uiso 1 1 calc R U H30B H 0.451145 0.092535 0.644397 0.055 Uiso 1 1 calc R U C31 C 0.5492(7) 0.2742(9) 0.6645(2) 0.060(2) Uani 1 1 d . . H31 H 0.458820 0.305845 0.680441 0.072 Uiso 1 1 calc R U O32 O 0.6194(6) 0.3806(5) 0.6462(2) 0.0626(14) Uani 1 1 d . . H32 H 0.570687 0.411136 0.623666 0.094 Uiso 1 1 calc R U C33 C 0.6480(8) 0.2035(11) 0.7009(3) 0.086(3) Uani 1 1 d . . O34 O 0.7706(7) 0.2313(11) 0.7070(3) 0.137(4) Uani 1 1 d . . O35 O 0.5705(7) 0.1289(8) 0.7277(2) 0.094(2) Uani 1 1 d . . C36 C 0.6555(13) 0.0511(12) 0.7644(3) 0.106(4) Uani 1 1 d . . H36A H 0.602367 -0.030257 0.773822 0.128 Uiso 1 1 calc R U H36B H 0.753352 0.026028 0.752865 0.128 Uiso 1 1 calc R U C37 C 0.6660(10) 0.1440(10) 0.8026(3) 0.082(3) Uani 1 1 d . . H37A H 0.721396 0.222395 0.792593 0.123 Uiso 1 1 calc R U H37B H 0.716001 0.101706 0.829013 0.123 Uiso 1 1 calc R U H37C H 0.567873 0.171299 0.812058 0.123 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 P1 0.0166(5) 0.0190(5) 0.0247(6) -0.0002(5) -0.0004(5) 0.0017(5) C1 0.017(2) 0.025(2) 0.030(3) 0.004(2) -0.0016(19) -0.0003(17) C2 0.023(2) 0.029(3) 0.033(3) -0.001(2) -0.001(2) 0.0004(19) C3 0.022(2) 0.044(3) 0.042(3) -0.001(3) 0.002(2) 0.006(2) C4 0.020(2) 0.038(3) 0.047(3) 0.000(2) 0.003(2) -0.002(2) C5 0.032(3) 0.044(3) 0.060(4) -0.010(3) 0.001(3) -0.014(3) C6 0.029(3) 0.029(3) 0.056(4) -0.009(2) 0.004(3) -0.001(2) C7 0.018(2) 0.017(2) 0.021(2) -0.0015(17) 0.0019(18) 0.0007(17) C8 0.028(2) 0.026(2) 0.026(2) -0.003(2) -0.001(2) -0.004(2) C9 0.029(3) 0.036(3) 0.025(2) -0.001(2) -0.006(2) -0.008(2) C10 0.035(3) 0.038(3) 0.026(3) 0.007(2) -0.007(2) 0.011(2) C11 0.033(3) 0.021(2) 0.033(3) 0.003(2) -0.002(2) 0.004(2) C12 0.024(2) 0.013(2) 0.026(2) -0.0023(17) -0.0015(19) 0.0029(17) C13 0.027(2) 0.022(2) 0.024(2) 0.0007(19) -0.0030(19) -0.0047(19) C14 0.039(3) 0.030(3) 0.032(3) -0.007(2) 0.002(2) 0.003(2) C15 0.052(4) 0.053(4) 0.042(4) -0.021(3) 0.015(3) 0.000(3) C16 0.071(5) 0.072(5) 0.027(3) -0.018(3) 0.012(3) -0.023(4) C17 0.052(4) 0.096(6) 0.026(3) -0.001(3) -0.008(3) -0.013(4) C18 0.038(3) 0.048(3) 0.031(3) 0.004(3) -0.002(2) 0.007(3) N21 0.0178(17) 0.0239(19) 0.033(2) 0.0000(18) -0.0002(18) 0.0031(16) C22 0.023(2) 0.023(2) 0.019(2) -0.0020(18) -0.0032(18) 0.0011(18) C23 0.024(2) 0.016(2) 0.032(3) -0.0012(18) -0.002(2) 0.0008(19) C24 0.020(2) 0.028(2) 0.027(2) -0.005(2) -0.0010(19) -0.0009(19) C25 0.030(3) 0.029(3) 0.025(2) -0.001(2) 0.001(2) -0.005(2) C26 0.037(3) 0.019(2) 0.029(3) -0.0011(19) 0.004(2) 0.003(2) C27 0.025(2) 0.028(2) 0.017(2) 0.0009(19) -0.0015(19) -0.0007(19) C28 0.035(3) 0.013(2) 0.035(3) 0.0031(19) 0.004(2) 0.0004(19) C29 0.041(3) 0.036(3) 0.043(3) -0.006(3) 0.015(3) 0.000(3) C30 0.039(3) 0.044(3) 0.055(4) 0.022(3) 0.010(3) 0.019(3) C31 0.026(3) 0.109(7) 0.044(4) 0.037(4) -0.011(3) -0.015(4) O32 0.047(3) 0.068(3) 0.073(4) 0.022(3) -0.021(3) -0.002(3) C33 0.025(3) 0.141(9) 0.092(6) 0.074(6) -0.010(4) -0.004(4) O34 0.041(3) 0.265(11) 0.105(5) 0.120(7) 0.001(4) 0.011(5) O35 0.067(4) 0.142(6) 0.073(4) 0.068(4) -0.018(3) -0.022(4) C36 0.127(9) 0.142(10) 0.049(5) 0.058(6) -0.039(6) -0.052(8) C37 0.075(6) 0.088(7) 0.083(7) 0.043(6) -0.011(5) 0.001(5) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 '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 N21 P1 C13 116.5(2) N21 P1 C1 105.6(2) C13 P1 C1 105.8(2) N21 P1 C7 114.4(2) C13 P1 C7 108.0(2) C1 P1 C7 105.8(2) C2 C1 C6 120.7(5) C2 C1 P1 119.8(4) C6 C1 P1 119.4(4) C1 C2 C3 119.6(5) C1 C2 H2 120.2 C3 C2 H2 120.2 C4 C3 C2 119.7(5) C4 C3 H3 120.2 C2 C3 H3 120.2 C5 C4 C3 120.8(5) C5 C4 H4 119.6 C3 C4 H4 119.6 C4 C5 C6 119.1(5) C4 C5 H5 120.4 C6 C5 H5 120.4 C1 C6 C5 120.2(5) C1 C6 H6 119.9 C5 C6 H6 119.9 C12 C7 C8 119.4(4) C12 C7 P1 122.4(4) C8 C7 P1 118.1(3) C9 C8 C7 120.1(5) C9 C8 H8 119.9 C7 C8 H8 119.9 C8 C9 C10 119.8(5) C8 C9 H9 120.1 C10 C9 H9 120.1 C11 C10 C9 120.1(5) C11 C10 H10 120.0 C9 C10 H10 120.0 C10 C11 C12 120.5(5) C10 C11 H11 119.7 C12 C11 H11 119.7 C11 C12 C7 120.0(4) C11 C12 H12 120.0 C7 C12 H12 120.0 C14 C13 C18 118.9(5) C14 C13 P1 124.4(4) C18 C13 P1 116.7(4) C13 C14 C15 120.7(6) C13 C14 H14 119.7 C15 C14 H14 119.7 C14 C15 C16 119.0(6) C14 C15 H15 120.5 C16 C15 H15 120.5 C17 C16 C15 120.4(6) C17 C16 H16 119.8 C15 C16 H16 119.8 C18 C17 C16 120.0(6) C18 C17 H17 120.0 C16 C17 H17 120.0 C17 C18 C13 121.1(6) C17 C18 H18 119.5 C13 C18 H18 119.5 C22 N21 P1 127.3(3) N21 C22 C23 124.8(4) N21 C22 C27 118.6(4) C23 C22 C27 116.6(4) C24 C23 C22 121.8(4) C24 C23 H23 119.1 C22 C23 H23 119.1 C23 C24 C25 120.6(5) C23 C24 H24 119.7 C25 C24 H24 119.7 C26 C25 C24 118.5(5) C26 C25 H25 120.8 C24 C25 H25 120.8 C27 C26 C25 122.0(5) C27 C26 H26 119.0 C25 C26 H26 119.0 C26 C27 C22 120.3(5) C26 C27 C28 120.3(4) C22 C27 C28 119.3(4) C29 C28 C27 122.1(5) C29 C28 C30 121.9(5) C27 C28 C30 116.0(5) C28 C29 H29A 120.0 C28 C29 H29B 120.0 H29A C29 H29B 120.0 C28 C30 C31 110.2(5) C28 C30 H30A 109.6 C31 C30 H30A 109.6 C28 C30 H30B 109.6 C31 C30 H30B 109.6 H30A C30 H30B 108.1 O32 C31 C33 110.2(5) O32 C31 C30 115.1(6) C33 C31 C30 105.3(7) O32 C31 H31 108.7 C33 C31 H31 108.7 C30 C31 H31 108.7 C31 O32 H32 109.5 O34 C33 O35 125.6(7) O34 C33 C31 123.2(8) O35 C33 C31 110.2(6) C33 O35 C36 115.4(7) C37 C36 O35 102.9(9) C37 C36 H36A 111.2 O35 C36 H36A 111.2 C37 C36 H36B 111.2 O35 C36 H36B 111.2 H36A C36 H36B 109.1 C36 C37 H37A 109.5 C36 C37 H37B 109.5 H37A C37 H37B 109.5 C36 C37 H37C 109.5 H37A C37 H37C 109.5 H37B C37 H37C 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance P1 N21 1.575(4) P1 C13 1.805(5) P1 C1 1.808(5) P1 C7 1.817(5) C1 C2 1.368(7) C1 C6 1.386(7) C2 C3 1.398(7) C2 H2 0.9500 C3 C4 1.392(8) C3 H3 0.9500 C4 C5 1.373(9) C4 H4 0.9500 C5 C6 1.400(8) C5 H5 0.9500 C6 H6 0.9500 C7 C12 1.390(6) C7 C8 1.400(6) C8 C9 1.382(7) C8 H8 0.9500 C9 C10 1.391(7) C9 H9 0.9500 C10 C11 1.376(7) C10 H10 0.9500 C11 C12 1.382(7) C11 H11 0.9500 C12 H12 0.9500 C13 C14 1.381(7) C13 C18 1.399(7) C14 C15 1.393(8) C14 H14 0.9500 C15 C16 1.395(10) C15 H15 0.9500 C16 C17 1.381(11) C16 H16 0.9500 C17 C18 1.363(9) C17 H17 0.9500 C18 H18 0.9500 N21 C22 1.394(6) C22 C23 1.409(7) C22 C27 1.421(6) C23 C24 1.382(7) C23 H23 0.9500 C24 C25 1.386(7) C24 H24 0.9500 C25 C26 1.382(7) C25 H25 0.9500 C26 C27 1.378(7) C26 H26 0.9500 C27 C28 1.486(7) C28 C29 1.327(8) C28 C30 1.520(8) C29 H29A 0.9500 C29 H29B 0.9500 C30 C31 1.563(11) C30 H30A 0.9900 C30 H30B 0.9900 C31 O32 1.355(8) C31 C33 1.551(9) C31 H31 1.0000 O32 H32 0.8400 C33 O34 1.170(10) C33 O35 1.288(9) O35 C36 1.521(10) C36 C37 1.439(14) C36 H36A 0.9900 C36 H36B 0.9900 C37 H37A 0.9800 C37 H37B 0.9800 C37 H37C 0.9800 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 N21 P1 C1 C2 28.1(5) C13 P1 C1 C2 152.1(4) C7 P1 C1 C2 -93.5(4) N21 P1 C1 C6 -155.4(4) C13 P1 C1 C6 -31.4(5) C7 P1 C1 C6 83.0(5) C6 C1 C2 C3 0.4(8) P1 C1 C2 C3 176.9(4) C1 C2 C3 C4 -1.3(8) C2 C3 C4 C5 1.2(9) C3 C4 C5 C6 -0.2(10) C2 C1 C6 C5 0.6(9) P1 C1 C6 C5 -175.9(5) C4 C5 C6 C1 -0.7(10) N21 P1 C7 C12 -175.2(4) C13 P1 C7 C12 53.4(5) C1 P1 C7 C12 -59.5(5) N21 P1 C7 C8 0.1(5) C13 P1 C7 C8 -131.3(4) C1 P1 C7 C8 115.8(4) C12 C7 C8 C9 -1.3(8) P1 C7 C8 C9 -176.8(4) C7 C8 C9 C10 -0.5(8) C8 C9 C10 C11 1.6(9) C9 C10 C11 C12 -0.8(8) C10 C11 C12 C7 -1.0(8) C8 C7 C12 C11 2.1(7) P1 C7 C12 C11 177.4(4) N21 P1 C13 C14 -120.7(5) C1 P1 C13 C14 122.5(5) C7 P1 C13 C14 9.6(5) N21 P1 C13 C18 59.4(5) C1 P1 C13 C18 -57.5(5) C7 P1 C13 C18 -170.4(4) C18 C13 C14 C15 1.1(9) P1 C13 C14 C15 -178.8(5) C13 C14 C15 C16 -1.2(10) C14 C15 C16 C17 0.7(11) C15 C16 C17 C18 -0.2(11) C16 C17 C18 C13 0.1(11) C14 C13 C18 C17 -0.6(9) P1 C13 C18 C17 179.4(5) C13 P1 N21 C22 57.8(5) C1 P1 N21 C22 174.8(4) C7 P1 N21 C22 -69.4(5) P1 N21 C22 C23 0.2(7) P1 N21 C22 C27 178.7(4) N21 C22 C23 C24 -177.5(5) C27 C22 C23 C24 3.9(7) C22 C23 C24 C25 -0.4(8) C23 C24 C25 C26 -1.6(8) C24 C25 C26 C27 -0.1(8) C25 C26 C27 C22 3.7(8) C25 C26 C27 C28 -179.9(5) N21 C22 C27 C26 175.9(4) C23 C22 C27 C26 -5.5(7) N21 C22 C27 C28 -0.6(7) C23 C22 C27 C28 178.1(4) C26 C27 C28 C29 103.6(6) C22 C27 C28 C29 -80.0(7) C26 C27 C28 C30 -74.9(6) C22 C27 C28 C30 101.5(6) C29 C28 C30 C31 118.5(6) C27 C28 C30 C31 -62.9(6) C28 C30 C31 O32 -56.4(7) C28 C30 C31 C33 -177.9(5) O32 C31 C33 O34 -8.0(16) C30 C31 C33 O34 116.7(13) O32 C31 C33 O35 161.3(9) C30 C31 C33 O35 -74.1(10) O34 C33 O35 C36 -12.4(19) C31 C33 O35 C36 178.6(9) C33 O35 C36 C37 86.3(12)