#------------------------------------------------------------------------------ #$Date: 2020-04-28 02:29:56 +0300 (Tue, 28 Apr 2020) $ #$Revision: 251204 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/04/7240416.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_7240416 loop_ _publ_author_name 'Zhang, Zhipeng' 'Yu, Yang' 'Xie, Yuxing' 'Hughes, Timothy' 'Xu, Jun' 'Huang, Fei' 'Huang, He' _publ_section_title ; Catalytic C−C Coupling of Diazo Compounds with Arylboronic Acids: Using Surface Modified Sewage Sludge as Greener Catalyst ; _journal_name_full 'Green Chemistry' _journal_paper_doi 10.1039/D0GC00317D _journal_year 2020 _chemical_formula_sum 'C11 H9 F O2' _chemical_formula_weight 192.18 _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 _audit_creation_method SHELXL-2013 _audit_update_record ; 2020-01-07 deposited with the CCDC. 2020-04-23 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 98.757(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 8.2958(8) _cell_length_b 7.8128(7) _cell_length_c 14.5059(16) _cell_measurement_reflns_used 4137 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 54.630 _cell_measurement_theta_min 6.958 _cell_volume 929.22(16) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' _computing_structure_solution 'SHELXS-97 (Sheldrick 2008)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.992 _diffrn_measured_fraction_theta_max 0.992 _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 0.0321 _diffrn_reflns_av_unetI/netI 0.0229 _diffrn_reflns_Laue_measured_fraction_full 0.992 _diffrn_reflns_Laue_measured_fraction_max 0.992 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 9686 _diffrn_reflns_point_group_measured_fraction_full 0.992 _diffrn_reflns_point_group_measured_fraction_max 0.992 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 25.499 _diffrn_reflns_theta_min 3.479 _exptl_absorpt_coefficient_mu 0.107 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_correction_T_min 0.6198 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details sadabs _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.374 _exptl_crystal_description prismatic _exptl_crystal_F_000 400 _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.160 _exptl_crystal_size_min 0.130 _refine_diff_density_max 0.180 _refine_diff_density_min -0.168 _refine_diff_density_rms 0.028 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 129 _refine_ls_number_reflns 1716 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.031 _refine_ls_R_factor_all 0.0586 _refine_ls_R_factor_gt 0.0487 _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^)+(0.0751P)^2^+0.1610P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1343 _refine_ls_wR_factor_ref 0.1458 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1377 _reflns_number_total 1716 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0gc00317d2.cif _cod_data_source_block mo_dd19317_0m _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 7240416 _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 0.979 _shelx_estimated_absorpt_t_max 0.986 _shelxl_version_number 2013-4 _shelx_res_file ; TITL mo_dd19317_0m_a.res in P2(1)/c CELL 0.71073 8.2958 7.8128 14.5059 90 98.757 90 ZERR 4 0.0008 0.0007 0.0016 0 0.003 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H F O UNIT 44 36 4 8 OMIT -1 3 1 OMIT -3.00 51.00 L.S. 10 ACTA BOND $H FMAP 2 PLAN 20 LIST 4 HTAB C5 F1_$2 HTAB C2 O1_$1 HTAB C5 F1_$2 HTAB C2 O1_$1 HTAB C5 F1_$2 EQIV $2 -x+1, y-1/2, -z+3/2 HTAB C2 O1_$1 EQIV $1 x, y+1, z conf htab mpla o2 c1 > c9 wpdb -1 size 0.20 0.16 0.13 HTAB C2 O1_$1 HTAB C5 F1_$2 TEMP 20 WGHT 0.075100 0.161000 FVAR 1.60387 F1 3 0.524640 0.619341 0.747977 11.00000 0.10896 0.12256 = 0.08895 -0.03338 0.03996 0.00864 O1 4 0.760246 0.158948 0.562534 11.00000 0.11515 0.05315 = 0.07728 0.01023 0.03262 0.00783 O2 4 0.785164 0.608552 0.426508 11.00000 0.07068 0.07476 = 0.07064 0.02312 0.01526 -0.01175 C1 1 0.721905 0.605502 0.508263 11.00000 0.05419 0.05485 = 0.06962 0.00568 0.00727 -0.00926 C2 1 0.670226 0.760349 0.540434 11.00000 0.07682 0.04949 = 0.10706 0.00286 0.00766 -0.00841 AFIX 43 H2 2 0.680234 0.860824 0.507396 11.00000 -1.20000 AFIX 0 C3 1 0.604702 0.763360 0.620951 11.00000 0.07460 0.06099 = 0.11013 -0.02607 0.00711 0.00091 AFIX 43 H3 2 0.569390 0.865832 0.643681 11.00000 -1.20000 AFIX 0 C4 1 0.591521 0.612673 0.668143 11.00000 0.06443 0.07964 = 0.07252 -0.02078 0.01630 -0.00313 C5 1 0.640778 0.459446 0.638459 11.00000 0.06249 0.06335 = 0.05913 -0.00362 0.01451 -0.00633 AFIX 43 H5 2 0.629372 0.359888 0.672012 11.00000 -1.20000 AFIX 0 C6 1 0.709025 0.454909 0.556284 11.00000 0.05058 0.05169 = 0.05235 0.00117 0.00894 -0.00581 C7 1 0.766010 0.294402 0.520425 11.00000 0.05990 0.05473 = 0.05362 0.00278 0.01004 -0.00195 C8 1 0.828322 0.306983 0.432832 11.00000 0.05514 0.07837 = 0.05079 -0.00007 0.01015 0.00057 C9 1 0.835387 0.459191 0.391047 11.00000 0.05145 0.09216 = 0.05439 0.00833 0.01050 -0.00545 C10 1 0.896370 0.493716 0.301325 11.00000 0.08021 0.15400 = 0.06022 0.02516 0.01976 -0.01286 AFIX 137 H10A 2 0.818367 0.452801 0.250371 11.00000 -1.50000 H10B 2 0.998461 0.435931 0.301194 11.00000 -1.50000 H10C 2 0.911545 0.614645 0.294642 11.00000 -1.50000 AFIX 0 C11 1 0.881826 0.145374 0.391158 11.00000 0.09058 0.10332 = 0.07370 -0.01496 0.02471 0.01559 AFIX 137 H11A 2 0.984782 0.109692 0.425102 11.00000 -1.50000 H11B 2 0.893043 0.165178 0.327128 11.00000 -1.50000 H11C 2 0.801985 0.057554 0.394502 11.00000 -1.50000 AFIX 0 HKLF 4 REM mo_dd19317_0m_a.res in P2(1)/c REM R1 = 0.0487 for 1377 Fo > 4sig(Fo) and 0.0586 for all 1716 data REM 129 parameters refined using 0 restraints END WGHT 0.0752 0.1611 REM Instructions for potential hydrogen bonds HTAB C2 O1_$1 HTAB C5 F1_$2 REM Highest difference peak 0.180, deepest hole -0.168, 1-sigma level 0.028 Q1 1 0.9930 0.1773 0.3679 11.00000 0.05 0.18 Q2 1 0.8050 0.5749 0.2612 11.00000 0.05 0.15 Q3 1 0.7935 0.1017 0.3397 11.00000 0.05 0.15 Q4 1 0.9073 0.0495 0.4609 11.00000 0.05 0.13 Q5 1 0.6938 0.7654 0.6015 11.00000 0.05 0.12 Q6 1 0.9908 0.5821 0.3177 11.00000 0.05 0.12 Q7 1 0.7592 0.3016 0.4647 11.00000 0.05 0.11 Q8 1 0.8105 0.3147 0.4814 11.00000 0.05 0.11 Q9 1 0.6985 0.4726 0.5996 11.00000 0.05 0.11 Q10 1 0.6837 0.5227 0.5112 11.00000 0.05 0.11 Q11 1 0.7370 0.6874 0.5427 11.00000 0.05 0.10 Q12 1 0.7839 0.3534 0.3980 11.00000 0.05 0.10 Q13 1 0.8818 0.3818 0.4275 11.00000 0.05 0.10 Q14 1 0.7570 0.5192 0.5465 11.00000 0.05 0.09 Q15 1 0.6550 0.6871 0.5208 11.00000 0.05 0.09 Q16 1 0.6541 0.6852 0.6627 11.00000 0.05 0.09 Q17 1 0.7709 0.3899 0.5533 11.00000 0.05 0.09 Q18 1 0.5689 0.5322 0.6439 11.00000 0.05 0.09 Q19 1 0.8751 0.3651 0.2425 11.00000 0.05 0.09 Q20 1 0.6932 0.8473 0.4557 11.00000 0.05 0.09 ; _shelx_res_checksum 37444 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 F1 F 0.52464(17) 0.61934(18) 0.74798(9) 0.1042(5) Uani 1 1 d . . . . . O1 O 0.76025(18) 0.15895(15) 0.56253(9) 0.0800(5) Uani 1 1 d . . . . . O2 O 0.78516(15) 0.60855(16) 0.42651(9) 0.0716(4) Uani 1 1 d . . . . . C1 C 0.72190(19) 0.6055(2) 0.50826(13) 0.0598(4) Uani 1 1 d . . . . . C2 C 0.6702(2) 0.7603(2) 0.54043(16) 0.0785(6) Uani 1 1 d . . . . . H2 H 0.6802 0.8608 0.5074 0.094 Uiso 1 1 calc R U . . . C3 C 0.6047(2) 0.7634(3) 0.62095(17) 0.0826(6) Uani 1 1 d . . . . . H3 H 0.5694 0.8658 0.6437 0.099 Uiso 1 1 calc R U . . . C4 C 0.5915(2) 0.6127(2) 0.66814(14) 0.0716(5) Uani 1 1 d . . . . . C5 C 0.64078(19) 0.4594(2) 0.63846(12) 0.0611(4) Uani 1 1 d . . . . . H5 H 0.6294 0.3599 0.6720 0.073 Uiso 1 1 calc R U . . . C6 C 0.70902(17) 0.45491(18) 0.55628(11) 0.0514(4) Uani 1 1 d . . . . . C7 C 0.76601(19) 0.29440(19) 0.52042(11) 0.0559(4) Uani 1 1 d . . . . . C8 C 0.82832(19) 0.3070(2) 0.43283(11) 0.0612(4) Uani 1 1 d . . . . . C9 C 0.83539(19) 0.4592(3) 0.39105(12) 0.0657(5) Uani 1 1 d . . . . . C10 C 0.8964(3) 0.4937(4) 0.30132(14) 0.0972(8) Uani 1 1 d . . . . . H10A H 0.8184 0.4528 0.2504 0.146 Uiso 1 1 calc R U . . . H10B H 0.9985 0.4359 0.3012 0.146 Uiso 1 1 calc R U . . . H10C H 0.9115 0.6146 0.2946 0.146 Uiso 1 1 calc R U . . . C11 C 0.8818(3) 0.1454(3) 0.39116(16) 0.0879(6) Uani 1 1 d . . . . . H11A H 0.9848 0.1097 0.4251 0.132 Uiso 1 1 calc R U . . . H11B H 0.8930 0.1652 0.3271 0.132 Uiso 1 1 calc R U . . . H11C H 0.8020 0.0576 0.3945 0.132 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 F1 0.1090(10) 0.1226(11) 0.0889(9) -0.0334(8) 0.0400(7) 0.0086(8) O1 0.1151(11) 0.0532(7) 0.0773(9) 0.0102(6) 0.0326(8) 0.0078(6) O2 0.0707(8) 0.0748(8) 0.0706(8) 0.0231(6) 0.0153(6) -0.0118(6) C1 0.0542(9) 0.0549(9) 0.0696(11) 0.0057(7) 0.0073(7) -0.0093(7) C2 0.0768(12) 0.0495(9) 0.1071(16) 0.0029(10) 0.0077(11) -0.0084(8) C3 0.0746(12) 0.0610(11) 0.1101(17) -0.0261(11) 0.0071(11) 0.0009(9) C4 0.0644(10) 0.0796(12) 0.0725(12) -0.0208(9) 0.0163(8) -0.0031(8) C5 0.0625(9) 0.0634(10) 0.0591(10) -0.0036(7) 0.0145(7) -0.0063(7) C6 0.0506(8) 0.0517(8) 0.0524(8) 0.0012(6) 0.0089(6) -0.0058(6) C7 0.0599(9) 0.0547(9) 0.0536(9) 0.0028(7) 0.0100(7) -0.0020(7) C8 0.0551(9) 0.0784(11) 0.0508(9) -0.0001(8) 0.0101(7) 0.0006(7) C9 0.0515(9) 0.0922(13) 0.0544(10) 0.0083(9) 0.0105(7) -0.0054(8) C10 0.0802(13) 0.154(2) 0.0602(12) 0.0252(13) 0.0198(10) -0.0129(13) C11 0.0906(14) 0.1033(15) 0.0737(13) -0.0150(11) 0.0247(10) 0.0156(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' F F 0.0171 0.0103 '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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 O2 C1 119.40(13) . . ? O2 C1 C6 121.46(15) . . ? O2 C1 C2 117.08(16) . . ? C6 C1 C2 121.46(18) . . ? C3 C2 C1 119.19(18) . . ? C3 C2 H2 120.4 . . ? C1 C2 H2 120.4 . . ? C2 C3 C4 119.00(18) . . ? C2 C3 H3 120.5 . . ? C4 C3 H3 120.5 . . ? C5 C4 F1 119.09(18) . . ? C5 C4 C3 123.18(19) . . ? F1 C4 C3 117.73(17) . . ? C4 C5 C6 118.33(17) . . ? C4 C5 H5 120.8 . . ? C6 C5 H5 120.8 . . ? C1 C6 C5 118.83(15) . . ? C1 C6 C7 119.82(15) . . ? C5 C6 C7 121.35(14) . . ? O1 C7 C8 122.85(15) . . ? O1 C7 C6 121.55(14) . . ? C8 C7 C6 115.60(14) . . ? C9 C8 C7 120.25(17) . . ? C9 C8 C11 122.01(17) . . ? C7 C8 C11 117.74(17) . . ? C8 C9 O2 123.44(15) . . ? C8 C9 C10 126.8(2) . . ? O2 C9 C10 109.74(18) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C8 C11 H11A 109.5 . . ? C8 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C8 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 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 F1 C4 1.359(2) . ? O1 C7 1.2265(19) . ? O2 C9 1.366(2) . ? O2 C1 1.368(2) . ? C1 C6 1.380(2) . ? C1 C2 1.388(3) . ? C2 C3 1.361(3) . ? C2 H2 0.9300 . ? C3 C4 1.375(3) . ? C3 H3 0.9300 . ? C4 C5 1.356(2) . ? C5 C6 1.396(2) . ? C5 H5 0.9300 . ? C6 C7 1.463(2) . ? C7 C8 1.446(2) . ? C8 C9 1.340(3) . ? C8 C11 1.496(3) . ? C9 C10 1.491(2) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C5 H5 F1 0.93 2.64 3.514(2) 157.0 2_646 C2 H2 O1 0.93 2.52 3.207(2) 131.1 1_565 C5 H5 F1 0.93 2.64 3.514(2) 157.0 2_646 C2 H2 O1 0.93 2.52 3.207(2) 131.1 1_565 C5 H5 F1 0.93 2.64 3.514(2) 157.0 2_646 C2 H2 O1 0.93 2.52 3.207(2) 131.1 1_565 C2 H2 O1 0.93 2.52 3.207(2) 131.1 1_565 C5 H5 F1 0.93 2.64 3.514(2) 157.0 2_646 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 C9 O2 C1 C6 0.6(2) . . . . ? C9 O2 C1 C2 -178.96(15) . . . . ? O2 C1 C2 C3 179.26(15) . . . . ? C6 C1 C2 C3 -0.3(3) . . . . ? C1 C2 C3 C4 0.0(3) . . . . ? C2 C3 C4 C5 0.0(3) . . . . ? C2 C3 C4 F1 -179.57(16) . . . . ? F1 C4 C5 C6 179.93(14) . . . . ? C3 C4 C5 C6 0.4(3) . . . . ? O2 C1 C6 C5 -178.87(13) . . . . ? C2 C1 C6 C5 0.7(2) . . . . ? O2 C1 C6 C7 0.9(2) . . . . ? C2 C1 C6 C7 -179.55(15) . . . . ? C4 C5 C6 C1 -0.7(2) . . . . ? C4 C5 C6 C7 179.53(14) . . . . ? C1 C6 C7 O1 178.12(16) . . . . ? C5 C6 C7 O1 -2.1(2) . . . . ? C1 C6 C7 C8 -2.0(2) . . . . ? C5 C6 C7 C8 177.73(13) . . . . ? O1 C7 C8 C9 -178.36(16) . . . . ? C6 C7 C8 C9 1.8(2) . . . . ? O1 C7 C8 C11 2.3(3) . . . . ? C6 C7 C8 C11 -177.56(14) . . . . ? C7 C8 C9 O2 -0.4(3) . . . . ? C11 C8 C9 O2 178.94(16) . . . . ? C7 C8 C9 C10 179.83(16) . . . . ? C11 C8 C9 C10 -0.9(3) . . . . ? C1 O2 C9 C8 -0.9(2) . . . . ? C1 O2 C9 C10 178.93(14) . . . . ?