#------------------------------------------------------------------------------ #$Date: 2019-10-15 02:55:52 +0300 (Tue, 15 Oct 2019) $ #$Revision: 219336 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/43/7124304.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_7124304 loop_ _publ_author_name 'Kim, Hyewon' 'Thombal, Raju S.' 'Khanal, Hari Datta' 'Lee, Yong Rok' _publ_section_title ; Rhodium(III)-catalyzed regioselective distal ortho C-H alkenylation of N-benzyl/furanylmethylpyrazoles directed by N-coordinating heterocycles ; _journal_name_full 'Chemical Communications' _journal_paper_doi 10.1039/C9CC06758B _journal_year 2019 _chemical_formula_sum 'C14 H14 N2 O2' _chemical_formula_weight 242.27 _chemical_melting_point 331 _chemical_name_systematic 'Methyl (E)-3-(2-((1H-pyrazol-1-yl)methyl)phenyl)acrylate' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2019-07-30 deposited with the CCDC. 2019-10-14 downloaded from the CCDC. ; _cell_angle_alpha 84.918(4) _cell_angle_beta 66.058(4) _cell_angle_gamma 61.274(4) _cell_formula_units_Z 2 _cell_length_a 8.868(5) _cell_length_b 8.948(5) _cell_length_c 10.107(6) _cell_measurement_reflns_used 3461 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 27.74 _cell_measurement_theta_min 2.79 _cell_volume 637.1(6) _computing_cell_refinement 'Bruker APEXIII' _computing_data_collection 'Bruker APEXIII' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics ORTEP _computing_publication_material CIFTAB _computing_structure_refinement SHELXL _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 173(2) _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.930 _diffrn_measurement_device_type 'Photon 100 CMOS detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0434 _diffrn_reflns_av_unetI/netI 0.0448 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.930 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 12629 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.930 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.449 _diffrn_reflns_theta_min 2.790 _diffrn_source 'fine-focus sealed tube' _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_correction_T_min 0.6507 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details SADABS _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.263 _exptl_crystal_description block _exptl_crystal_F_000 256 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: Hexane/EtOAc' _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.200 _refine_diff_density_max 0.200 _refine_diff_density_min -0.174 _refine_diff_density_rms 0.035 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.095 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 164 _refine_ls_number_reflns 2984 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.095 _refine_ls_R_factor_all 0.1219 _refine_ls_R_factor_gt 0.0664 _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^)+(0.0519P)^2^+0.1623P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1336 _refine_ls_wR_factor_ref 0.1556 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1783 _reflns_number_total 2984 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9cc06758b2.cif _cod_data_source_block 71a_re_a _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_absorpt_correction_type' value 'MULTI-SCAN' changed to 'multi-scan' according to /home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26. Automatic conversion script Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas ; _cod_database_code 7124304 _shelx_shelxl_version_number 2018/3 _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 0.983 _shelx_estimated_absorpt_t_max 0.983 _shelx_res_file ; TITL 71a_re_a.res in P-1 71a_re_a.res created by SHELXL-2018/3 at 14:40:48 on 30-Jul-2019 REM Old TITL 71a_re in P-1 REM SHELXT solution in P-1: R1 0.199, Rweak 0.033, Alpha 0.044 REM 0.000 for 0 systematic absences, Orientation as input REM Formula found by SHELXT: C14 N3 O CELL 0.71073 8.8684 8.9476 10.1070 84.918 66.058 61.274 ZERR 2.000 0.0052 0.0052 0.0059 0.004 0.004 0.004 LATT 1 SFAC C H N O UNIT 28 28 4 4 ACTA TEMP -100 SIZE 0.20 0.20 0.20 L.S. 10 BOND $H LIST 4 FMAP 2 PLAN 20 WGHT 0.051900 0.162300 FVAR 0.76614 N1 3 0.001161 0.577686 0.647511 11.00000 0.04463 0.04902 = 0.05008 0.00431 -0.02193 -0.01814 C1 1 0.780693 -0.122585 0.075473 11.00000 0.08100 0.10300 = 0.08383 -0.03935 -0.01844 -0.02602 AFIX 137 H1A 2 0.670528 -0.112470 0.066088 11.00000 -1.50000 H1B 2 0.866422 -0.243640 0.075643 11.00000 -1.50000 H1C 2 0.846833 -0.078567 -0.006942 11.00000 -1.50000 AFIX 0 O1 4 0.718855 -0.023350 0.211345 11.00000 0.05376 0.09898 = 0.08164 -0.03934 -0.01439 -0.01659 O2 4 1.016974 -0.135317 0.179032 11.00000 0.04988 0.08516 = 0.09315 -0.01807 -0.01414 -0.00239 N2 3 -0.063440 0.743141 0.621935 11.00000 0.05625 0.05224 = 0.06820 0.01278 -0.02700 -0.02326 C2 1 0.851596 -0.038432 0.250030 11.00000 0.04529 0.05119 = 0.06599 0.00437 -0.01528 -0.01345 C5 1 0.510904 0.296478 0.595710 11.00000 0.04529 0.04866 = 0.04877 0.00924 -0.02077 -0.02448 C4 1 0.594615 0.181139 0.460765 11.00000 0.04406 0.05313 = 0.05855 0.00347 -0.02235 -0.02025 AFIX 43 H4 2 0.509418 0.186273 0.424002 11.00000 -1.20000 AFIX 0 C3 1 0.774979 0.071581 0.385525 11.00000 0.04634 0.06216 = 0.06345 0.00203 -0.02175 -0.01879 AFIX 43 H3 2 0.861812 0.063290 0.421811 11.00000 -1.20000 AFIX 0 C8 1 0.354578 0.518336 0.850280 11.00000 0.07234 0.07638 = 0.05166 0.00019 -0.02801 -0.03954 AFIX 43 H8 2 0.301386 0.594488 0.936080 11.00000 -1.20000 AFIX 0 C7 1 0.539607 0.388416 0.799335 11.00000 0.06776 0.08615 = 0.06309 0.01458 -0.03895 -0.04512 AFIX 43 H7 2 0.613642 0.373298 0.851004 11.00000 -1.20000 AFIX 0 C6 1 0.617466 0.279997 0.672848 11.00000 0.04767 0.06597 = 0.06635 0.01197 -0.02941 -0.02641 AFIX 43 H6 2 0.746069 0.192351 0.637393 11.00000 -1.20000 AFIX 0 C9 1 0.246143 0.537671 0.775970 11.00000 0.05047 0.06026 = 0.05001 -0.00005 -0.01996 -0.02202 AFIX 43 H9 2 0.118624 0.627669 0.811633 11.00000 -1.20000 AFIX 0 C10 1 0.320312 0.428061 0.650463 11.00000 0.04411 0.04916 = 0.04291 0.00706 -0.01891 -0.02243 C11 1 0.199773 0.449945 0.570301 11.00000 0.04333 0.05926 = 0.04658 -0.00360 -0.01908 -0.01515 AFIX 23 H11A 2 0.251675 0.483745 0.473264 11.00000 -1.20000 H11B 2 0.208777 0.337828 0.554311 11.00000 -1.20000 AFIX 0 C12 1 -0.133943 0.553894 0.753652 11.00000 0.05374 0.05697 = 0.06331 0.01613 -0.02493 -0.02558 AFIX 43 H12 2 -0.119829 0.448606 0.790251 11.00000 -1.20000 AFIX 0 C13 1 -0.295796 0.709321 0.799423 11.00000 0.04546 0.06650 = 0.06167 0.00377 -0.01526 -0.02024 AFIX 43 H13 2 -0.416722 0.734821 0.872965 11.00000 -1.20000 AFIX 0 C14 1 -0.244676 0.821006 0.715168 11.00000 0.05257 0.04863 = 0.07315 0.00032 -0.02459 -0.01361 AFIX 43 H14 2 -0.329307 0.940028 0.722857 11.00000 -1.20000 CONF MERG 2 AFIX 0 HKLF 4 REM 71a_re_a.res in P-1 REM wR2 = 0.1556, GooF = S = 1.095, Restrained GooF = 1.095 for all data REM R1 = 0.0664 for 1783 Fo > 4sig(Fo) and 0.1219 for all 2984 data REM 164 parameters refined using 0 restraints END WGHT 0.0520 0.1624 REM Highest difference peak 0.200, deepest hole -0.174, 1-sigma level 0.035 Q1 1 0.7635 0.0625 0.1706 11.00000 0.05 0.20 Q2 1 0.5409 0.2473 0.5360 11.00000 0.05 0.13 Q3 1 0.1323 0.7004 0.7691 11.00000 0.05 0.13 Q4 1 0.2429 0.3860 0.4854 11.00000 0.05 0.12 Q5 1 0.7084 -0.0288 0.0200 11.00000 0.05 0.12 Q6 1 -0.0677 0.3737 0.7214 11.00000 0.05 0.12 Q7 1 0.5123 0.2918 0.3768 11.00000 0.05 0.12 Q8 1 -0.0308 0.7440 0.5162 11.00000 0.05 0.11 Q9 1 0.7758 -0.2815 0.1166 11.00000 0.05 0.11 Q10 1 0.3050 0.4968 0.6875 11.00000 0.05 0.11 Q11 1 -0.1262 0.7980 0.7208 11.00000 0.05 0.10 Q12 1 0.7411 0.0960 0.6734 11.00000 0.05 0.10 Q13 1 0.0406 0.7023 0.5083 11.00000 0.05 0.10 Q14 1 0.9742 -0.0415 0.1407 11.00000 0.05 0.10 Q15 1 0.8202 0.2841 0.5492 11.00000 0.05 0.10 Q16 1 0.0404 0.7322 0.6760 11.00000 0.05 0.10 Q17 1 0.7619 -0.0766 0.2541 11.00000 0.05 0.10 Q18 1 0.6527 -0.1917 0.1344 11.00000 0.05 0.09 Q19 1 0.4184 0.3547 0.6200 11.00000 0.05 0.09 Q20 1 0.5664 0.3410 0.5903 11.00000 0.05 0.09 ; _shelx_res_checksum 75191 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -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 N1 N 0.0012(2) 0.5777(2) 0.64751(17) 0.0491(4) Uani 1 1 d . . C1 C 0.7807(4) -0.1226(4) 0.0755(3) 0.1001(10) Uani 1 1 d . . H1A H 0.670528 -0.112470 0.066088 0.150 Uiso 1 1 calc R U H1B H 0.866422 -0.243640 0.075643 0.150 Uiso 1 1 calc R U H1C H 0.846833 -0.078567 -0.006942 0.150 Uiso 1 1 calc R U O1 O 0.7189(2) -0.0234(2) 0.21135(19) 0.0890(6) Uani 1 1 d . . O2 O 1.0170(2) -0.1353(2) 0.1790(2) 0.0938(6) Uani 1 1 d . . N2 N -0.0634(3) 0.7431(2) 0.6219(2) 0.0603(5) Uani 1 1 d . . C2 C 0.8516(3) -0.0384(3) 0.2500(2) 0.0615(6) Uani 1 1 d . . C5 C 0.5109(3) 0.2965(3) 0.5957(2) 0.0466(5) Uani 1 1 d . . C4 C 0.5946(3) 0.1811(3) 0.4608(2) 0.0528(5) Uani 1 1 d . . H4 H 0.509418 0.186273 0.424002 0.063 Uiso 1 1 calc R U C3 C 0.7750(3) 0.0716(3) 0.3855(2) 0.0608(6) Uani 1 1 d . . H3 H 0.861812 0.063290 0.421811 0.073 Uiso 1 1 calc R U C8 C 0.3546(3) 0.5183(3) 0.8503(2) 0.0638(6) Uani 1 1 d . . H8 H 0.301386 0.594488 0.936080 0.077 Uiso 1 1 calc R U C7 C 0.5396(3) 0.3884(3) 0.7993(2) 0.0648(6) Uani 1 1 d . . H7 H 0.613642 0.373298 0.851004 0.078 Uiso 1 1 calc R U C6 C 0.6175(3) 0.2800(3) 0.6728(2) 0.0587(6) Uani 1 1 d . . H6 H 0.746069 0.192351 0.637393 0.070 Uiso 1 1 calc R U C9 C 0.2461(3) 0.5377(3) 0.7760(2) 0.0557(6) Uani 1 1 d . . H9 H 0.118624 0.627669 0.811633 0.067 Uiso 1 1 calc R U C10 C 0.3203(3) 0.4281(3) 0.6505(2) 0.0453(5) Uani 1 1 d . . C11 C 0.1998(3) 0.4499(3) 0.5703(2) 0.0534(5) Uani 1 1 d . . H11A H 0.251675 0.483745 0.473264 0.064 Uiso 1 1 calc R U H11B H 0.208777 0.337828 0.554311 0.064 Uiso 1 1 calc R U C12 C -0.1339(3) 0.5539(3) 0.7537(2) 0.0591(6) Uani 1 1 d . . H12 H -0.119829 0.448606 0.790251 0.071 Uiso 1 1 calc R U C13 C -0.2958(3) 0.7093(3) 0.7994(2) 0.0634(6) Uani 1 1 d . . H13 H -0.416722 0.734821 0.872965 0.076 Uiso 1 1 calc R U C14 C -0.2447(3) 0.8210(3) 0.7152(3) 0.0632(6) Uani 1 1 d . . H14 H -0.329307 0.940028 0.722857 0.076 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 N1 0.0446(9) 0.0490(11) 0.0501(9) 0.0043(8) -0.0219(8) -0.0181(8) C1 0.0810(19) 0.103(2) 0.0838(19) -0.0394(17) -0.0184(16) -0.0260(17) O1 0.0538(10) 0.0990(14) 0.0816(12) -0.0393(10) -0.0144(9) -0.0166(10) O2 0.0499(10) 0.0852(13) 0.0932(13) -0.0181(11) -0.0141(9) -0.0024(9) N2 0.0562(11) 0.0522(12) 0.0682(12) 0.0128(9) -0.0270(10) -0.0233(9) C2 0.0453(13) 0.0512(14) 0.0660(14) 0.0044(11) -0.0153(11) -0.0134(11) C5 0.0453(11) 0.0487(12) 0.0488(11) 0.0092(9) -0.0208(9) -0.0245(10) C4 0.0441(11) 0.0531(13) 0.0586(12) 0.0035(10) -0.0223(10) -0.0203(10) C3 0.0463(12) 0.0622(15) 0.0634(14) 0.0020(12) -0.0218(11) -0.0188(11) C8 0.0723(16) 0.0764(17) 0.0517(12) 0.0002(11) -0.0280(12) -0.0395(14) C7 0.0678(15) 0.0861(18) 0.0631(14) 0.0146(13) -0.0390(12) -0.0451(14) C6 0.0477(12) 0.0660(15) 0.0664(14) 0.0120(12) -0.0294(11) -0.0264(11) C9 0.0505(12) 0.0603(14) 0.0500(12) -0.0001(10) -0.0200(10) -0.0220(11) C10 0.0441(11) 0.0492(12) 0.0429(10) 0.0071(9) -0.0189(9) -0.0224(9) C11 0.0433(11) 0.0593(14) 0.0466(11) -0.0036(10) -0.0191(9) -0.0151(10) C12 0.0537(13) 0.0570(14) 0.0633(13) 0.0161(11) -0.0249(11) -0.0256(11) C13 0.0455(12) 0.0665(15) 0.0617(13) 0.0038(12) -0.0153(10) -0.0202(12) C14 0.0526(13) 0.0486(13) 0.0731(15) 0.0003(11) -0.0246(12) -0.0136(11) 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C12 N1 N2 112.02(17) C12 N1 C11 126.97(19) N2 N1 C11 120.90(17) O1 C1 H1A 109.5 O1 C1 H1B 109.5 H1A C1 H1B 109.5 O1 C1 H1C 109.5 H1A C1 H1C 109.5 H1B C1 H1C 109.5 C2 O1 C1 117.52(19) C14 N2 N1 103.87(18) O2 C2 O1 121.9(2) O2 C2 C3 124.9(2) O1 C2 C3 113.21(18) C6 C5 C10 118.14(19) C6 C5 C4 121.30(19) C10 C5 C4 120.56(18) C3 C4 C5 127.0(2) C3 C4 H4 116.5 C5 C4 H4 116.5 C4 C3 C2 124.9(2) C4 C3 H3 117.6 C2 C3 H3 117.6 C7 C8 C9 119.8(2) C7 C8 H8 120.1 C9 C8 H8 120.1 C8 C7 C6 119.9(2) C8 C7 H7 120.1 C6 C7 H7 120.1 C7 C6 C5 121.5(2) C7 C6 H6 119.3 C5 C6 H6 119.3 C8 C9 C10 121.3(2) C8 C9 H9 119.4 C10 C9 H9 119.4 C9 C10 C5 119.41(18) C9 C10 C11 120.81(18) C5 C10 C11 119.78(17) N1 C11 C10 113.78(16) N1 C11 H11A 108.8 C10 C11 H11A 108.8 N1 C11 H11B 108.8 C10 C11 H11B 108.8 H11A C11 H11B 107.7 N1 C12 C13 107.2(2) N1 C12 H12 126.4 C13 C12 H12 126.4 C12 C13 C14 104.6(2) C12 C13 H13 127.7 C14 C13 H13 127.7 N2 C14 C13 112.3(2) N2 C14 H14 123.9 C13 C14 H14 123.9 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance N1 C12 1.339(3) N1 N2 1.350(2) N1 C11 1.458(2) C1 O1 1.453(3) C1 H1A 0.9800 C1 H1B 0.9800 C1 H1C 0.9800 O1 C2 1.330(3) O2 C2 1.205(3) N2 C14 1.329(3) C2 C3 1.465(3) C5 C6 1.402(3) C5 C10 1.412(3) C5 C4 1.472(3) C4 C3 1.317(3) C4 H4 0.9500 C3 H3 0.9500 C8 C7 1.377(3) C8 C9 1.386(3) C8 H8 0.9500 C7 C6 1.383(3) C7 H7 0.9500 C6 H6 0.9500 C9 C10 1.388(3) C9 H9 0.9500 C10 C11 1.520(3) C11 H11A 0.9900 C11 H11B 0.9900 C12 C13 1.365(3) C12 H12 0.9500 C13 C14 1.379(3) C13 H13 0.9500 C14 H14 0.9500 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 C12 N1 N2 C14 -0.7(2) C11 N1 N2 C14 -177.14(18) C1 O1 C2 O2 -2.8(4) C1 O1 C2 C3 177.8(2) C6 C5 C4 C3 -10.8(3) C10 C5 C4 C3 168.8(2) C5 C4 C3 C2 -178.8(2) O2 C2 C3 C4 177.9(2) O1 C2 C3 C4 -2.8(3) C9 C8 C7 C6 1.3(4) C8 C7 C6 C5 -1.4(3) C10 C5 C6 C7 0.2(3) C4 C5 C6 C7 179.8(2) C7 C8 C9 C10 0.1(3) C8 C9 C10 C5 -1.3(3) C8 C9 C10 C11 179.69(19) C6 C5 C10 C9 1.1(3) C4 C5 C10 C9 -178.45(18) C6 C5 C10 C11 -179.83(18) C4 C5 C10 C11 0.6(3) C12 N1 C11 C10 -83.7(3) N2 N1 C11 C10 92.2(2) C9 C10 C11 N1 -7.5(3) C5 C10 C11 N1 173.51(18) N2 N1 C12 C13 0.8(2) C11 N1 C12 C13 176.96(19) N1 C12 C13 C14 -0.5(3) N1 N2 C14 C13 0.4(3) C12 C13 C14 N2 0.1(3)