#------------------------------------------------------------------------------ #$Date: 2016-08-07 11:06:42 +0300 (Sun, 07 Aug 2016) $ #$Revision: 185159 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/54/32/1543271.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_1543271 loop_ _publ_author_name 'Brachet, Etienne' 'Marzo, Leyre' 'Selkti, Mohamed' 'K\"onig, Burkhard' 'Belmont, Philippe' _publ_section_title ; Visible light amination/Smiles cascade: access to phthalazine derivatives ; _journal_issue 8 _journal_name_full 'Chem. Sci.' _journal_page_first 5002 _journal_paper_doi 10.1039/C6SC01095D _journal_volume 7 _journal_year 2016 _chemical_formula_sum 'C21 H16 N2' _chemical_formula_weight 296.36 _chemical_name_systematic 1-Benzhydrylphthalazine _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_creation_method SHELXL-2013 _audit_update_record ; 2016-01-27 deposited with the CCDC. 2016-05-06 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 108.362(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 8.8549(4) _cell_length_b 18.0318(9) _cell_length_c 10.1285(5) _cell_measurement_reflns_used 9976 _cell_measurement_temperature 100(1) _cell_measurement_theta_max 30.49 _cell_measurement_theta_min 2.40 _cell_volume 1534.88(13) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _diffrn_ambient_temperature 100(1) _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.987 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0381 _diffrn_reflns_av_unetI/netI 0.0285 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.987 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 21391 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.987 _diffrn_reflns_theta_full 25.000 _diffrn_reflns_theta_max 30.532 _diffrn_reflns_theta_min 2.259 _diffrn_source 'sealed tube' _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_T_max 0.8842 _exptl_absorpt_correction_T_min 0.7461 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details SADABS _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.282 _exptl_crystal_F_000 624 _exptl_crystal_size_max 0.110 _exptl_crystal_size_mid 0.090 _exptl_crystal_size_min 0.060 _refine_diff_density_max 0.442 _refine_diff_density_min -0.218 _refine_diff_density_rms 0.050 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 208 _refine_ls_number_reflns 4628 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.027 _refine_ls_R_factor_all 0.0574 _refine_ls_R_factor_gt 0.0468 _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^)+(0.0586P)^2^+0.6589P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1165 _refine_ls_wR_factor_ref 0.1245 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3906 _reflns_number_total 4628 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c6sc01095d2.cif _cod_data_source_block 2195GuillotICMMO _cod_depositor_comments 'Adding full bibliography for 1543271.cif.' _cod_original_cell_volume 1534.87(13) _cod_database_code 1543271 _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_min 0.992 _shelx_estimated_absorpt_t_max 0.995 _shelxl_version_number 2013-4 _shelx_res_file ; TITL 2195_0m in P2(1)/n CELL 0.71073 8.8549 18.0318 10.1285 90.000 108.362 90.000 ZERR 4.00 0.0004 0.0009 0.0005 0.000 0.002 0.000 LATT 1 SYMM 1/2 - X, 1/2 + Y, 1/2 - Z SFAC C H N UNIT 84 64 8 MERG 2 FMAP 2 PLAN 20 SIZE 0.060 0.090 0.110 ACTA 50.00 BOND WPDB -2 L.S. 4 TEMP 20.00 WGHT 0.058600 0.658900 FVAR 0.21442 MOLE 1 N2 3 0.670995 0.207602 0.517226 11.00000 0.02135 0.02650 = 0.01424 0.00151 0.00521 -0.00224 N1 3 0.675959 0.242041 0.397159 11.00000 0.01789 0.02124 = 0.01480 0.00076 0.00533 -0.00167 C2 1 0.474925 0.158416 0.258274 11.00000 0.01303 0.01532 = 0.01645 0.00138 0.00556 0.00143 C1 1 0.582204 0.220122 0.275354 11.00000 0.01337 0.01548 = 0.01507 0.00126 0.00525 0.00151 C9 1 0.594742 0.261893 0.148596 11.00000 0.01442 0.01587 = 0.01454 0.00176 0.00366 -0.00097 AFIX 13 H9 2 0.486872 0.266283 0.082975 11.00000 -1.20000 AFIX 0 C7 1 0.467579 0.124557 0.381238 11.00000 0.01592 0.01764 = 0.01812 0.00213 0.00663 0.00116 C10 1 0.659885 0.340107 0.182520 11.00000 0.01924 0.01555 = 0.01599 0.00137 0.00732 -0.00039 C3 1 0.381801 0.129503 0.128494 11.00000 0.01708 0.01963 = 0.01741 0.00050 0.00460 -0.00090 AFIX 43 H3 2 0.383399 0.151894 0.046229 11.00000 -1.20000 AFIX 0 C8 1 0.569941 0.153555 0.508267 11.00000 0.02067 0.02407 = 0.01629 0.00322 0.00732 -0.00001 AFIX 43 H8 2 0.564721 0.132672 0.590675 11.00000 -1.20000 AFIX 0 C16 1 0.693739 0.219138 0.075234 11.00000 0.01668 0.01739 = 0.01458 -0.00156 0.00577 -0.00484 C4 1 0.288838 0.068014 0.124846 11.00000 0.01927 0.02281 = 0.02275 -0.00220 0.00370 -0.00368 AFIX 43 H4 2 0.230577 0.047877 0.039454 11.00000 -1.20000 AFIX 0 C21 1 0.681313 0.237473 -0.061644 11.00000 0.02266 0.02495 = 0.01516 -0.00027 0.00444 -0.00831 AFIX 43 H21 2 0.610203 0.274146 -0.107434 11.00000 -1.20000 AFIX 0 C6 1 0.366292 0.063311 0.375446 11.00000 0.02030 0.02153 = 0.02349 0.00485 0.00909 -0.00113 AFIX 43 H6 2 0.357978 0.042444 0.456842 11.00000 -1.20000 AFIX 0 C15 1 0.559219 0.401178 0.146961 11.00000 0.02221 0.01985 = 0.02354 0.00276 0.00806 0.00355 AFIX 43 H15 2 0.451015 0.394224 0.102430 11.00000 -1.20000 AFIX 0 C5 1 0.280403 0.035004 0.248404 11.00000 0.02049 0.02020 = 0.03091 0.00156 0.00800 -0.00484 AFIX 43 H5 2 0.216055 -0.006312 0.243716 11.00000 -1.20000 AFIX 0 C11 1 0.822002 0.351890 0.247942 11.00000 0.01935 0.01857 = 0.02145 -0.00008 0.00703 -0.00149 AFIX 43 H11 2 0.890802 0.311541 0.270383 11.00000 -1.20000 AFIX 0 C12 1 0.881887 0.423073 0.279952 11.00000 0.02460 0.02204 = 0.02472 -0.00290 0.01004 -0.00676 AFIX 43 H12 2 0.989946 0.430115 0.325031 11.00000 -1.20000 AFIX 0 C17 1 0.802377 0.164770 0.141490 11.00000 0.02375 0.02170 = 0.02217 0.00188 0.01180 0.00148 AFIX 43 H17 2 0.813161 0.152072 0.233003 11.00000 -1.20000 AFIX 0 C13 1 0.780715 0.483780 0.244777 11.00000 0.03720 0.01714 = 0.02981 -0.00276 0.01699 -0.00547 AFIX 43 H13 2 0.820720 0.531520 0.266060 11.00000 -1.20000 AFIX 0 C19 1 0.881292 0.147594 -0.062967 11.00000 0.03281 0.02798 = 0.03370 -0.01040 0.02245 -0.00975 AFIX 43 H19 2 0.943749 0.123883 -0.108721 11.00000 -1.20000 AFIX 0 C20 1 0.773708 0.201698 -0.130485 11.00000 0.03019 0.03269 = 0.01798 -0.00737 0.01157 -0.01648 AFIX 43 H20 2 0.763253 0.214121 -0.222057 11.00000 -1.20000 AFIX 0 C14 1 0.619694 0.472878 0.177743 11.00000 0.03499 0.01739 = 0.03136 0.00277 0.01444 0.00426 AFIX 43 H14 2 0.551738 0.513451 0.153200 11.00000 -1.20000 AFIX 0 C18 1 0.895400 0.129008 0.072689 11.00000 0.02975 0.02541 = 0.03646 0.00061 0.02015 0.00395 AFIX 43 H18 2 0.967184 0.092525 0.118238 11.00000 -1.20000 AFIX 0 HKLF 4 REM 2195_0m in P2(1)/n REM R1 = 0.0468 for 3906 Fo > 4sig(Fo) and 0.0574 for all 4628 data REM 208 parameters refined using 0 restraints END WGHT 0.0581 0.6667 REM Highest difference peak 0.442, deepest hole -0.218, 1-sigma level 0.050 Q1 1 0.4718 0.1391 0.3216 11.00000 0.05 0.44 Q2 1 0.6020 0.2399 0.2154 11.00000 0.05 0.40 Q3 1 0.7001 0.2275 0.0109 11.00000 0.05 0.37 Q4 1 0.8719 0.1418 0.0044 11.00000 0.05 0.37 Q5 1 0.5180 0.1913 0.2677 11.00000 0.05 0.37 Q6 1 0.5157 0.1406 0.4409 11.00000 0.05 0.36 Q7 1 0.6563 0.2418 0.1218 11.00000 0.05 0.34 Q8 1 0.2940 0.0545 0.1936 11.00000 0.05 0.32 Q9 1 0.6337 0.2990 0.1703 11.00000 0.05 0.32 Q10 1 0.4144 0.0965 0.3805 11.00000 0.05 0.31 Q11 1 0.8522 0.1534 0.1057 11.00000 0.05 0.30 Q12 1 0.3414 0.0961 0.1282 11.00000 0.05 0.30 Q13 1 0.4394 0.1425 0.1988 11.00000 0.05 0.30 Q14 1 0.6266 0.2301 0.3343 11.00000 0.05 0.29 Q15 1 0.8481 0.3885 0.2551 11.00000 0.05 0.29 Q16 1 0.6175 0.3714 0.1501 11.00000 0.05 0.28 Q17 1 0.5990 0.4358 0.1675 11.00000 0.05 0.28 Q18 1 0.6682 0.2241 0.4560 11.00000 0.05 0.26 Q19 1 0.3247 0.0547 0.3099 11.00000 0.05 0.26 Q20 1 0.7210 0.2177 -0.1017 11.00000 0.05 0.24 ; _shelx_res_checksum 3078 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 N2 N 0.67100(12) 0.20760(6) 0.51723(9) 0.0208(2) Uani 1 1 d . . N1 N 0.67596(11) 0.24204(5) 0.39716(9) 0.01793(19) Uani 1 1 d . . C2 C 0.47493(12) 0.15842(6) 0.25827(10) 0.01472(19) Uani 1 1 d . . C1 C 0.58220(12) 0.22012(6) 0.27535(10) 0.01446(19) Uani 1 1 d . . C9 C 0.59474(12) 0.26189(6) 0.14860(10) 0.01515(19) Uani 1 1 d . . H9 H 0.4869 0.2663 0.0830 0.018 Uiso 1 1 calc R U C7 C 0.46758(12) 0.12456(6) 0.38124(11) 0.0169(2) Uani 1 1 d . . C10 C 0.65989(13) 0.34011(6) 0.18252(11) 0.0165(2) Uani 1 1 d . . C3 C 0.38180(13) 0.12950(6) 0.12849(11) 0.0182(2) Uani 1 1 d . . H3 H 0.3834 0.1519 0.0462 0.022 Uiso 1 1 calc R U C8 C 0.56994(13) 0.15355(6) 0.50827(11) 0.0200(2) Uani 1 1 d . . H8 H 0.5647 0.1327 0.5907 0.024 Uiso 1 1 calc R U C16 C 0.69374(12) 0.21914(6) 0.07523(10) 0.0160(2) Uani 1 1 d . . C4 C 0.28884(13) 0.06801(6) 0.12485(12) 0.0223(2) Uani 1 1 d . . H4 H 0.2306 0.0479 0.0395 0.027 Uiso 1 1 calc R U C21 C 0.68131(14) 0.23747(7) -0.06164(11) 0.0213(2) Uani 1 1 d . . H21 H 0.6102 0.2741 -0.1074 0.026 Uiso 1 1 calc R U C6 C 0.36629(13) 0.06331(6) 0.37545(12) 0.0213(2) Uani 1 1 d . . H6 H 0.3580 0.0424 0.4568 0.026 Uiso 1 1 calc R U C15 C 0.55922(14) 0.40118(6) 0.14696(12) 0.0217(2) Uani 1 1 d . . H15 H 0.4510 0.3942 0.1024 0.026 Uiso 1 1 calc R U C5 C 0.28040(14) 0.03500(7) 0.24840(13) 0.0239(2) Uani 1 1 d . . H5 H 0.2161 -0.0063 0.2437 0.029 Uiso 1 1 calc R U C11 C 0.82200(13) 0.35189(6) 0.24794(12) 0.0196(2) Uani 1 1 d . . H11 H 0.8908 0.3115 0.2704 0.024 Uiso 1 1 calc R U C12 C 0.88189(15) 0.42307(7) 0.27995(12) 0.0233(2) Uani 1 1 d . . H12 H 0.9899 0.4301 0.3250 0.028 Uiso 1 1 calc R U C17 C 0.80238(14) 0.16477(6) 0.14149(12) 0.0215(2) Uani 1 1 d . . H17 H 0.8132 0.1521 0.2330 0.026 Uiso 1 1 calc R U C13 C 0.78071(16) 0.48378(7) 0.24478(13) 0.0265(3) Uani 1 1 d . . H13 H 0.8207 0.5315 0.2661 0.032 Uiso 1 1 calc R U C19 C 0.88129(16) 0.14759(7) -0.06297(14) 0.0287(3) Uani 1 1 d . . H19 H 0.9437 0.1239 -0.1087 0.034 Uiso 1 1 calc R U C20 C 0.77371(15) 0.20170(7) -0.13048(12) 0.0260(3) Uani 1 1 d . . H20 H 0.7633 0.2141 -0.2221 0.031 Uiso 1 1 calc R U C14 C 0.61969(16) 0.47288(7) 0.17774(14) 0.0270(3) Uani 1 1 d . . H14 H 0.5517 0.5135 0.1532 0.032 Uiso 1 1 calc R U C18 C 0.89540(16) 0.12901(7) 0.07269(14) 0.0283(3) Uani 1 1 d . . H18 H 0.9672 0.0925 0.1182 0.034 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 N2 0.0214(5) 0.0265(5) 0.0142(4) 0.0015(3) 0.0052(3) -0.0022(4) N1 0.0179(4) 0.0212(4) 0.0148(4) 0.0008(3) 0.0053(3) -0.0017(3) C2 0.0130(4) 0.0153(4) 0.0164(4) 0.0014(3) 0.0056(4) 0.0014(3) C1 0.0134(4) 0.0155(4) 0.0151(4) 0.0013(3) 0.0053(4) 0.0015(3) C9 0.0144(4) 0.0159(4) 0.0145(4) 0.0018(3) 0.0037(4) -0.0010(3) C7 0.0159(4) 0.0176(5) 0.0181(5) 0.0021(4) 0.0066(4) 0.0012(4) C10 0.0192(5) 0.0156(4) 0.0160(4) 0.0014(3) 0.0073(4) -0.0004(4) C3 0.0171(5) 0.0196(5) 0.0174(5) 0.0005(4) 0.0046(4) -0.0009(4) C8 0.0207(5) 0.0241(5) 0.0163(5) 0.0032(4) 0.0073(4) 0.0000(4) C16 0.0167(5) 0.0174(5) 0.0146(4) -0.0016(3) 0.0058(4) -0.0048(4) C4 0.0193(5) 0.0228(5) 0.0227(5) -0.0022(4) 0.0037(4) -0.0037(4) C21 0.0227(5) 0.0250(5) 0.0152(5) -0.0003(4) 0.0044(4) -0.0083(4) C6 0.0203(5) 0.0215(5) 0.0235(5) 0.0049(4) 0.0091(4) -0.0011(4) C15 0.0222(5) 0.0199(5) 0.0235(5) 0.0028(4) 0.0081(4) 0.0035(4) C5 0.0205(5) 0.0202(5) 0.0309(6) 0.0016(4) 0.0080(5) -0.0048(4) C11 0.0193(5) 0.0186(5) 0.0215(5) -0.0001(4) 0.0070(4) -0.0015(4) C12 0.0246(5) 0.0220(5) 0.0247(5) -0.0029(4) 0.0100(4) -0.0068(4) C17 0.0237(5) 0.0217(5) 0.0222(5) 0.0019(4) 0.0118(4) 0.0015(4) C13 0.0372(7) 0.0171(5) 0.0298(6) -0.0028(4) 0.0170(5) -0.0055(5) C19 0.0328(6) 0.0280(6) 0.0337(6) -0.0104(5) 0.0225(5) -0.0097(5) C20 0.0302(6) 0.0327(6) 0.0180(5) -0.0074(4) 0.0116(5) -0.0165(5) C14 0.0350(7) 0.0174(5) 0.0314(6) 0.0028(4) 0.0144(5) 0.0043(5) C18 0.0298(6) 0.0254(6) 0.0365(7) 0.0006(5) 0.0202(5) 0.0039(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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C8 N2 N1 119.09(9) C1 N1 N2 120.47(9) C7 C2 C3 119.16(9) C7 C2 C1 116.26(9) C3 C2 C1 124.56(9) N1 C1 C2 123.00(9) N1 C1 C9 116.82(9) C2 C1 C9 120.16(9) C10 C9 C1 113.04(8) C10 C9 C16 110.09(8) C1 C9 C16 111.51(8) C2 C7 C6 120.56(10) C2 C7 C8 116.62(9) C6 C7 C8 122.78(10) C15 C10 C11 118.82(10) C15 C10 C9 120.59(10) C11 C10 C9 120.58(9) C4 C3 C2 119.45(10) N2 C8 C7 124.43(10) C17 C16 C21 118.23(10) C17 C16 C9 122.56(9) C21 C16 C9 119.13(10) C3 C4 C5 121.05(11) C20 C21 C16 120.92(11) C5 C6 C7 119.18(10) C10 C15 C14 120.38(11) C6 C5 C4 120.51(10) C12 C11 C10 120.81(10) C11 C12 C13 120.08(11) C16 C17 C18 120.89(11) C14 C13 C12 119.66(11) C18 C19 C20 119.66(11) C19 C20 C21 120.10(11) C13 C14 C15 120.23(11) C19 C18 C17 120.18(12) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance N2 C8 1.3067(15) N2 N1 1.3785(12) N1 C1 1.3123(13) C2 C7 1.4068(14) C2 C3 1.4130(14) C2 C1 1.4376(14) C1 C9 1.5224(14) C9 C10 1.5215(14) C9 C16 1.5249(14) C7 C6 1.4122(15) C7 C8 1.4197(15) C10 C15 1.3909(15) C10 C11 1.3949(15) C3 C4 1.3745(15) C16 C17 1.3893(15) C16 C21 1.3955(14) C4 C5 1.4089(17) C21 C20 1.3896(17) C6 C5 1.3704(17) C15 C14 1.3965(16) C11 C12 1.3876(15) C12 C13 1.3881(17) C17 C18 1.3934(16) C13 C14 1.3866(19) C19 C18 1.3812(19) C19 C20 1.384(2)